diff --git a/README.md b/README.md
index aecc6a5..2e5f616 100644
--- a/README.md
+++ b/README.md
@@ -69,6 +69,10 @@ Dart implementation of the protocol, and the terminal is
   password.
 - Customizable on-screen key row with modifiers, arrows, function keys, key
   repeat, latching modifiers, and your own text snippets and control-key combos.
+- Upload key: pick phone files, photos, or videos, stream them to the machine
+  over SFTP into `~/.conduit/uploads/<date>/`, and insert the shell-quoted
+  remote path into the terminal, with per-machine directory and optional
+  cleanup of Conduit's own old uploads.
 - Saved global and per-machine snippets from the key row, with hidden snippets
   for passwords or secrets and optional per-machine run-on-connect snippets.
 - Optional device-auth app lock for protecting saved machines and credentials.
diff --git a/lib/core/presentation/theme_sheet.dart b/lib/core/presentation/theme_sheet.dart
index fa66ad0..7da1637 100644
--- a/lib/core/presentation/theme_sheet.dart
+++ b/lib/core/presentation/theme_sheet.dart
@@ -1078,6 +1078,7 @@ IconData _keyboardActionIcon(TerminalKeyboardAction action) {
     TerminalKeyboardAction.tmuxMenu => Icons.view_quilt_rounded,
     TerminalKeyboardAction.snippets => Icons.snippet_folder_rounded,
     TerminalKeyboardAction.compose => Icons.edit_note_rounded,
+    TerminalKeyboardAction.upload => Icons.upload_file_rounded,
   };
 }
 
diff --git a/lib/core/theme/app_palette.dart b/lib/core/theme/app_palette.dart
index fc88815..c7a2762 100644
--- a/lib/core/theme/app_palette.dart
+++ b/lib/core/theme/app_palette.dart
@@ -18,6 +18,12 @@ enum AppPalette {
   palenight,
   synthwave,
   githubDark,
+  horizon,
+  iceberg,
+  sonokai,
+  zenburn,
+  carbonfox,
+  poimandres,
 }
 
 /// To add a palette: add a value to [AppPalette], then add its `PaletteSpec`
@@ -1094,5 +1100,275 @@ extension AppPaletteDetails on AppPalette {
       ),
       terminalLight: _lightFallbackTerminal,
     ),
+    AppPalette.horizon => const PaletteSpec(
+      label: 'Horizon',
+      caption: 'Warm dusk pinks and teals',
+      accent: Color(0xFFE95678),
+      accentSecondary: Color(0xFF26BBD9),
+      canvas: Color(0xFF16161C),
+      panel: Color(0xFF1C1E26),
+      panelElevated: Color(0xFF232530),
+      hairline: Color(0xFF2E303E),
+      border: Color(0xFF3A3D4D),
+      foreground: Color(0xFFD5D8DA),
+      mutedForeground: Color(0xFF9DA0A2),
+      subtleForeground: Color(0xFF6C6F93),
+      success: Color(0xFF29D398),
+      warning: Color(0xFFFAB795),
+      danger: Color(0xFFE95678),
+      canvasLight: Color(0xFFFDF0ED),
+      foregroundLight: Color(0xFF1C1E26),
+      terminalDark: TerminalTheme(
+        cursor: Color(0xFFE95678),
+        selection: Color(0x662E303E),
+        foreground: Color(0xFFD5D8DA),
+        background: Color(0xFF16161C),
+        black: Color(0xFF16161C),
+        red: Color(0xFFE95678),
+        green: Color(0xFF29D398),
+        yellow: Color(0xFFFAB795),
+        blue: Color(0xFF26BBD9),
+        magenta: Color(0xFFEE64AC),
+        cyan: Color(0xFF59E1E3),
+        white: Color(0xFFD5D8DA),
+        brightBlack: Color(0xFF6C6F93),
+        brightRed: Color(0xFFEC6A88),
+        brightGreen: Color(0xFF3FDAA4),
+        brightYellow: Color(0xFFFBC3A7),
+        brightBlue: Color(0xFF3FC4DE),
+        brightMagenta: Color(0xFFF075B5),
+        brightCyan: Color(0xFF6BE4E6),
+        brightWhite: Color(0xFFE5E5E5),
+        searchHitBackground: Color(0xFFFAB795),
+        searchHitBackgroundCurrent: Color(0xFF29D398),
+        searchHitForeground: Color(0xFF16161C),
+      ),
+      terminalLight: _lightFallbackTerminal,
+    ),
+    AppPalette.iceberg => const PaletteSpec(
+      label: 'Iceberg',
+      caption: 'Cool bluish depths',
+      accent: Color(0xFF84A0C6),
+      accentSecondary: Color(0xFFA093C7),
+      canvas: Color(0xFF101219),
+      panel: Color(0xFF161821),
+      panelElevated: Color(0xFF1E2132),
+      hairline: Color(0xFF272C42),
+      border: Color(0xFF33374C),
+      foreground: Color(0xFFC6C8D1),
+      mutedForeground: Color(0xFF8389A3),
+      subtleForeground: Color(0xFF6B7089),
+      success: Color(0xFFB4BE82),
+      warning: Color(0xFFE2A478),
+      danger: Color(0xFFE27878),
+      canvasLight: Color(0xFFE8E9EC),
+      foregroundLight: Color(0xFF33374C),
+      terminalDark: TerminalTheme(
+        cursor: Color(0xFFC6C8D1),
+        selection: Color(0x661E2132),
+        foreground: Color(0xFFC6C8D1),
+        background: Color(0xFF101219),
+        black: Color(0xFF1E2132),
+        red: Color(0xFFE27878),
+        green: Color(0xFFB4BE82),
+        yellow: Color(0xFFE2A478),
+        blue: Color(0xFF84A0C6),
+        magenta: Color(0xFFA093C7),
+        cyan: Color(0xFF89B8C2),
+        white: Color(0xFFC6C8D1),
+        brightBlack: Color(0xFF6B7089),
+        brightRed: Color(0xFFE98989),
+        brightGreen: Color(0xFFC0CA8E),
+        brightYellow: Color(0xFFE9B189),
+        brightBlue: Color(0xFF91ACD1),
+        brightMagenta: Color(0xFFADA0D3),
+        brightCyan: Color(0xFF95C4CE),
+        brightWhite: Color(0xFFD2D4DE),
+        searchHitBackground: Color(0xFFE2A478),
+        searchHitBackgroundCurrent: Color(0xFF84A0C6),
+        searchHitForeground: Color(0xFF101219),
+      ),
+      terminalLight: _lightFallbackTerminal,
+    ),
+    AppPalette.sonokai => const PaletteSpec(
+      label: 'Sonokai',
+      caption: 'High-contrast vivid shades',
+      accent: Color(0xFF9ED072),
+      accentSecondary: Color(0xFFB39DF3),
+      canvas: Color(0xFF22242A),
+      panel: Color(0xFF2C2E34),
+      panelElevated: Color(0xFF33353F),
+      hairline: Color(0xFF3B3E48),
+      border: Color(0xFF45484F),
+      foreground: Color(0xFFE2E2E3),
+      mutedForeground: Color(0xFF9DA0A8),
+      subtleForeground: Color(0xFF7F8490),
+      success: Color(0xFF9ED072),
+      warning: Color(0xFFE7C664),
+      danger: Color(0xFFFC5D7C),
+      canvasLight: Color(0xFFF4F3F1),
+      foregroundLight: Color(0xFF33353F),
+      terminalDark: TerminalTheme(
+        cursor: Color(0xFFE2E2E3),
+        selection: Color(0x66414550),
+        foreground: Color(0xFFE2E2E3),
+        background: Color(0xFF22242A),
+        black: Color(0xFF181A1C),
+        red: Color(0xFFFC5D7C),
+        green: Color(0xFF9ED072),
+        yellow: Color(0xFFE7C664),
+        blue: Color(0xFF76CCE0),
+        magenta: Color(0xFFB39DF3),
+        cyan: Color(0xFF76CCE0),
+        white: Color(0xFFE2E2E3),
+        brightBlack: Color(0xFF7F8490),
+        brightRed: Color(0xFFFC5D7C),
+        brightGreen: Color(0xFF9ED072),
+        brightYellow: Color(0xFFE7C664),
+        brightBlue: Color(0xFF76CCE0),
+        brightMagenta: Color(0xFFB39DF3),
+        brightCyan: Color(0xFF76CCE0),
+        brightWhite: Color(0xFFF4F3F1),
+        searchHitBackground: Color(0xFFE7C664),
+        searchHitBackgroundCurrent: Color(0xFF9ED072),
+        searchHitForeground: Color(0xFF22242A),
+      ),
+      terminalLight: _lightFallbackTerminal,
+    ),
+    AppPalette.zenburn => const PaletteSpec(
+      label: 'Zenburn',
+      caption: 'Low-contrast classic calm',
+      accent: Color(0xFFF0DFAF),
+      accentSecondary: Color(0xFF8CD0D3),
+      canvas: Color(0xFF313131),
+      panel: Color(0xFF3F3F3F),
+      panelElevated: Color(0xFF494949),
+      hairline: Color(0xFF525252),
+      border: Color(0xFF5F5F5F),
+      foreground: Color(0xFFDCDCCC),
+      mutedForeground: Color(0xFFA8A897),
+      subtleForeground: Color(0xFF709080),
+      success: Color(0xFF60B48A),
+      warning: Color(0xFFF0DFAF),
+      danger: Color(0xFFDCA3A3),
+      canvasLight: Color(0xFFF2F1E9),
+      foregroundLight: Color(0xFF3F3F3F),
+      terminalDark: TerminalTheme(
+        cursor: Color(0xFFDCDCCC),
+        selection: Color(0x66709080),
+        foreground: Color(0xFFDCDCCC),
+        background: Color(0xFF313131),
+        black: Color(0xFF1E2320),
+        red: Color(0xFF705050),
+        green: Color(0xFF60B48A),
+        yellow: Color(0xFFDFAF8F),
+        blue: Color(0xFF506070),
+        magenta: Color(0xFFDC8CC3),
+        cyan: Color(0xFF8CD0D3),
+        white: Color(0xFFDCDCCC),
+        brightBlack: Color(0xFF709080),
+        brightRed: Color(0xFFDCA3A3),
+        brightGreen: Color(0xFFC3BF9F),
+        brightYellow: Color(0xFFF0DFAF),
+        brightBlue: Color(0xFF94BFF3),
+        brightMagenta: Color(0xFFEC93D3),
+        brightCyan: Color(0xFF93E0E3),
+        brightWhite: Color(0xFFFFFFFF),
+        searchHitBackground: Color(0xFFF0DFAF),
+        searchHitBackgroundCurrent: Color(0xFF93E0E3),
+        searchHitForeground: Color(0xFF313131),
+      ),
+      terminalLight: _lightFallbackTerminal,
+    ),
+    AppPalette.carbonfox => const PaletteSpec(
+      label: 'Carbonfox',
+      caption: 'Carbon black, neon glow',
+      accent: Color(0xFF78A9FF),
+      accentSecondary: Color(0xFFBE95FF),
+      canvas: Color(0xFF0C0C0C),
+      panel: Color(0xFF161616),
+      panelElevated: Color(0xFF252525),
+      hairline: Color(0xFF2A2A2A),
+      border: Color(0xFF3C3C3C),
+      foreground: Color(0xFFF2F4F8),
+      mutedForeground: Color(0xFFB6B8BB),
+      subtleForeground: Color(0xFF7B7C7E),
+      success: Color(0xFF25BE6A),
+      warning: Color(0xFF08BDBA),
+      danger: Color(0xFFEE5396),
+      canvasLight: Color(0xFFF4F4F5),
+      foregroundLight: Color(0xFF161616),
+      terminalDark: TerminalTheme(
+        cursor: Color(0xFFF2F4F8),
+        selection: Color(0x662A2A2A),
+        foreground: Color(0xFFF2F4F8),
+        background: Color(0xFF0C0C0C),
+        black: Color(0xFF282828),
+        red: Color(0xFFEE5396),
+        green: Color(0xFF25BE6A),
+        yellow: Color(0xFF08BDBA),
+        blue: Color(0xFF78A9FF),
+        magenta: Color(0xFFBE95FF),
+        cyan: Color(0xFF33B1FF),
+        white: Color(0xFFDFDFE0),
+        brightBlack: Color(0xFF484848),
+        brightRed: Color(0xFFF16DA6),
+        brightGreen: Color(0xFF46C880),
+        brightYellow: Color(0xFF2DC7C4),
+        brightBlue: Color(0xFF8CB6FF),
+        brightMagenta: Color(0xFFC8A5FF),
+        brightCyan: Color(0xFF52BDFF),
+        brightWhite: Color(0xFFE4E4E5),
+        searchHitBackground: Color(0xFF08BDBA),
+        searchHitBackgroundCurrent: Color(0xFF78A9FF),
+        searchHitForeground: Color(0xFF0C0C0C),
+      ),
+      terminalLight: _lightFallbackTerminal,
+    ),
+    AppPalette.poimandres => const PaletteSpec(
+      label: 'Poimandres',
+      caption: 'Minimal teal on deep slate',
+      accent: Color(0xFF5DE4C7),
+      accentSecondary: Color(0xFF89DDFF),
+      canvas: Color(0xFF171922),
+      panel: Color(0xFF1B1E28),
+      panelElevated: Color(0xFF252B37),
+      hairline: Color(0xFF2C3341),
+      border: Color(0xFF3A4150),
+      foreground: Color(0xFFE4F0FB),
+      mutedForeground: Color(0xFFA6ACCD),
+      subtleForeground: Color(0xFF767C9D),
+      success: Color(0xFF5DE4C7),
+      warning: Color(0xFFFFFAC2),
+      danger: Color(0xFFD0679D),
+      canvasLight: Color(0xFFEFF3F9),
+      foregroundLight: Color(0xFF1B1E28),
+      terminalDark: TerminalTheme(
+        cursor: Color(0xFF5DE4C7),
+        selection: Color(0x66303340),
+        foreground: Color(0xFFE4F0FB),
+        background: Color(0xFF171922),
+        black: Color(0xFF1B1E28),
+        red: Color(0xFFD0679D),
+        green: Color(0xFF5DE4C7),
+        yellow: Color(0xFFFFFAC2),
+        blue: Color(0xFF89DDFF),
+        magenta: Color(0xFFFCC5E9),
+        cyan: Color(0xFFADD7FF),
+        white: Color(0xFFFFFFFF),
+        brightBlack: Color(0xFF767C9D),
+        brightRed: Color(0xFFD0679D),
+        brightGreen: Color(0xFF5DE4C7),
+        brightYellow: Color(0xFFFFFAC2),
+        brightBlue: Color(0xFF89DDFF),
+        brightMagenta: Color(0xFFFCC5E9),
+        brightCyan: Color(0xFFADD7FF),
+        brightWhite: Color(0xFFFFFFFF),
+        searchHitBackground: Color(0xFFFFFAC2),
+        searchHitBackgroundCurrent: Color(0xFF5DE4C7),
+        searchHitForeground: Color(0xFF171922),
+      ),
+      terminalLight: _lightFallbackTerminal,
+    ),
   };
 }
diff --git a/lib/core/theme/terminal_appearance.dart b/lib/core/theme/terminal_appearance.dart
index 3b1078e..0f7fff1 100644
--- a/lib/core/theme/terminal_appearance.dart
+++ b/lib/core/theme/terminal_appearance.dart
@@ -79,6 +79,7 @@ enum TerminalKeyboardAction {
   tmuxMenu,
   snippets,
   compose,
+  upload,
 }
 
 enum TerminalKeyboardItemKind { builtIn, customText, customControl }
@@ -170,6 +171,7 @@ const defaultTerminalKeyboardActions = [
   TerminalKeyboardAction.tmuxScrollback,
   TerminalKeyboardAction.tmuxMenu,
   TerminalKeyboardAction.snippets,
+  TerminalKeyboardAction.upload,
   TerminalKeyboardAction.fullscreen,
 ];
 
@@ -262,6 +264,7 @@ const defaultTerminalKeyboardItems = [
   TerminalKeyboardItem.builtIn(TerminalKeyboardAction.tmuxScrollback),
   TerminalKeyboardItem.builtIn(TerminalKeyboardAction.tmuxMenu),
   TerminalKeyboardItem.builtIn(TerminalKeyboardAction.snippets),
+  TerminalKeyboardItem.builtIn(TerminalKeyboardAction.upload),
   TerminalKeyboardItem.builtIn(TerminalKeyboardAction.fullscreen),
 ];
 
@@ -383,5 +386,6 @@ extension TerminalKeyboardActionDetails on TerminalKeyboardAction {
     TerminalKeyboardAction.tmuxMenu => 'Tmux+',
     TerminalKeyboardAction.snippets => 'Snip',
     TerminalKeyboardAction.compose => 'Compose',
+    TerminalKeyboardAction.upload => 'Upload',
   };
 }
diff --git a/lib/features/hosts/domain/saved_host.dart b/lib/features/hosts/domain/saved_host.dart
index 55af2cb..c5a623e 100644
--- a/lib/features/hosts/domain/saved_host.dart
+++ b/lib/features/hosts/domain/saved_host.dart
@@ -148,6 +148,8 @@ class SavedHost {
     this.tmuxStartDirectory = '',
     this.snippets = const [],
     this.connectSnippetId = '',
+    this.uploadDirectory = '',
+    this.uploadCleanupDays,
     this.lastConnectedAt,
     this.isLocal = false,
   });
@@ -188,6 +190,15 @@ class SavedHost {
   final String tmuxStartDirectory;
   final List<TerminalSnippet> snippets;
   final String connectSnippetId;
+
+  /// Remote directory for phone-file uploads. Empty means the default
+  /// `~/.conduit/uploads/<date>`; may be absolute or `~/`-relative.
+  final String uploadDirectory;
+
+  /// Age in days after which Conduit-uploaded files are deleted on the next
+  /// upload. Null disables automatic cleanup (the default).
+  final int? uploadCleanupDays;
+
   final DateTime? lastConnectedAt;
   final bool isLocal;
 
@@ -261,6 +272,9 @@ class SavedHost {
     String? tmuxStartDirectory,
     List<TerminalSnippet>? snippets,
     String? connectSnippetId,
+    String? uploadDirectory,
+    int? uploadCleanupDays,
+    bool clearUploadCleanupDays = false,
     DateTime? lastConnectedAt,
     bool clearLastConnectedAt = false,
     bool? isLocal,
@@ -292,6 +306,10 @@ class SavedHost {
       tmuxStartDirectory: tmuxStartDirectory ?? this.tmuxStartDirectory,
       snippets: snippets ?? this.snippets,
       connectSnippetId: connectSnippetId ?? this.connectSnippetId,
+      uploadDirectory: uploadDirectory ?? this.uploadDirectory,
+      uploadCleanupDays: clearUploadCleanupDays
+          ? null
+          : uploadCleanupDays ?? this.uploadCleanupDays,
       lastConnectedAt: clearLastConnectedAt
           ? null
           : lastConnectedAt ?? this.lastConnectedAt,
@@ -332,6 +350,8 @@ class SavedHost {
       'tmuxStartDirectory': tmuxStartDirectory,
       'snippets': [for (final snippet in snippets) snippet.toJson()],
       'connectSnippetId': connectSnippetId,
+      'uploadDirectory': uploadDirectory,
+      'uploadCleanupDays': uploadCleanupDays,
       'lastConnectedAt': lastConnectedAt?.toIso8601String(),
       'isLocal': isLocal,
     };
@@ -386,6 +406,11 @@ class SavedHost {
           .whereType<TerminalSnippet>()
           .toList(growable: false),
       connectSnippetId: json['connectSnippetId'] as String? ?? '',
+      uploadDirectory: (json['uploadDirectory'] as String?)?.trim() ?? '',
+      uploadCleanupDays: switch (json['uploadCleanupDays']) {
+        final int days when days > 0 => days,
+        _ => null,
+      },
       lastConnectedAt: lastConnectedAtRaw == null
           ? null
           : DateTime.tryParse(lastConnectedAtRaw),
diff --git a/lib/features/hosts/presentation/host_form_page.dart b/lib/features/hosts/presentation/host_form_page.dart
index 05a4799..119d9ee 100644
--- a/lib/features/hosts/presentation/host_form_page.dart
+++ b/lib/features/hosts/presentation/host_form_page.dart
@@ -51,11 +51,13 @@ class _HostFormPageState extends State<HostFormPage> {
     text: defaultTmuxSessionName,
   );
   final _tmuxStartDirectoryController = TextEditingController();
+  final _uploadDirectoryController = TextEditingController();
   final FocusNode _tagFocusNode = FocusNode();
   SshAuthMethod _authMethod = SshAuthMethod.password;
   bool _showPassword = false;
   bool _showPassphrase = false;
   bool _useMosh = false;
+  int? _uploadCleanupDays;
   bool _predictiveEchoEnabled = false;
   bool _externalAuthOfferKey = true;
   bool _forwardAgent = false;
@@ -116,6 +118,8 @@ class _HostFormPageState extends State<HostFormPage> {
       _tmuxStartDirectoryController.text = host.tmuxStartDirectory;
       _snippets = List<TerminalSnippet>.from(host.snippets);
       _connectSnippetId = host.connectSnippetId;
+      _uploadDirectoryController.text = host.uploadDirectory;
+      _uploadCleanupDays = host.uploadCleanupDays;
     }
     _keyInspection = _cheapPreview();
     WidgetsBinding.instance.addPostFrameCallback((_) {
@@ -196,6 +200,7 @@ class _HostFormPageState extends State<HostFormPage> {
     _moshPortsController.dispose();
     _tmuxSessionNameController.dispose();
     _tmuxStartDirectoryController.dispose();
+    _uploadDirectoryController.dispose();
     super.dispose();
   }
 
@@ -290,10 +295,12 @@ class _HostFormPageState extends State<HostFormPage> {
               moshPortsController: _moshPortsController,
               tmuxSessionNameController: _tmuxSessionNameController,
               tmuxStartDirectoryController: _tmuxStartDirectoryController,
+              uploadDirectoryController: _uploadDirectoryController,
               useMosh: _useMosh,
               predictiveEchoEnabled: _predictiveEchoEnabled,
               startTmuxOnConnect: _startTmuxOnConnect,
               tmuxPrefixKey: _tmuxPrefixKey,
+              uploadCleanupDays: _uploadCleanupDays,
               snippets: _snippets,
               connectSnippetId: _connectSnippetId,
               timeoutValidator: _validateTimeout,
@@ -312,6 +319,8 @@ class _HostFormPageState extends State<HostFormPage> {
                   setState(() => _startTmuxOnConnect = value),
               onTmuxPrefixKeyChanged: (value) =>
                   setState(() => _tmuxPrefixKey = value),
+              onUploadCleanupDaysChanged: (value) =>
+                  setState(() => _uploadCleanupDays = value),
               onSnippetsChanged: (snippets) => setState(() {
                 _snippets = snippets;
                 if (!_snippets.any(
@@ -717,6 +726,8 @@ class _HostFormPageState extends State<HostFormPage> {
           ? defaultTmuxSessionName
           : _tmuxSessionNameController.text.trim(),
       tmuxStartDirectory: _tmuxStartDirectoryController.text.trim(),
+      uploadDirectory: _uploadDirectoryController.text.trim(),
+      uploadCleanupDays: _uploadCleanupDays,
       snippets: List<TerminalSnippet>.unmodifiable(_snippets),
       connectSnippetId:
           _snippets.any((snippet) => snippet.id == _connectSnippetId)
diff --git a/lib/features/hosts/presentation/hosts_page.dart b/lib/features/hosts/presentation/hosts_page.dart
index b33c1f5..79f3a22 100644
--- a/lib/features/hosts/presentation/hosts_page.dart
+++ b/lib/features/hosts/presentation/hosts_page.dart
@@ -23,6 +23,7 @@ import 'package:conduit/features/local_shell/presentation/local_shell_setup_page
 import 'package:conduit/features/local_shell/presentation/widgets/local_shell_section.dart';
 import 'package:conduit/features/sftp/domain/file_export.dart';
 import 'package:conduit/features/sftp/domain/sftp_repository.dart';
+import 'package:conduit/features/sftp/domain/upload_manifest.dart';
 import 'package:conduit/features/sftp/presentation/sftp_browser_page.dart';
 import 'package:conduit/features/terminal/domain/host_key_prompt.dart';
 import 'package:conduit/features/terminal/domain/host_key_verifier.dart';
@@ -47,6 +48,7 @@ class HostsPage extends StatefulWidget {
     required this.hostKeyVerifier,
     required this.promptCoordinator,
     required this.sftpRepository,
+    required this.uploadManifestRepository,
     required this.backupService,
     required this.fileExport,
     super.key,
@@ -61,6 +63,7 @@ class HostsPage extends StatefulWidget {
   final HostKeyVerifier hostKeyVerifier;
   final HostKeyPromptCoordinator promptCoordinator;
   final SftpRepository sftpRepository;
+  final UploadManifestRepository uploadManifestRepository;
   final AppBackupService backupService;
   final FileExport fileExport;
 
@@ -440,6 +443,8 @@ class _HostsPageState extends State<HostsPage> {
         builder: (_) => TerminalPage(
           workspace: widget.workspaceController,
           themeController: widget.themeController,
+          sftpRepository: widget.sftpRepository,
+          uploadManifestRepository: widget.uploadManifestRepository,
         ),
       ),
     );
diff --git a/lib/features/hosts/presentation/widgets/host_form_sections.dart b/lib/features/hosts/presentation/widgets/host_form_sections.dart
index f9111cd..bace466 100644
--- a/lib/features/hosts/presentation/widgets/host_form_sections.dart
+++ b/lib/features/hosts/presentation/widgets/host_form_sections.dart
@@ -299,10 +299,12 @@ class HostAdvancedSection extends StatelessWidget {
     required this.moshPortsController,
     required this.tmuxSessionNameController,
     required this.tmuxStartDirectoryController,
+    required this.uploadDirectoryController,
     required this.useMosh,
     required this.predictiveEchoEnabled,
     required this.startTmuxOnConnect,
     required this.tmuxPrefixKey,
+    required this.uploadCleanupDays,
     required this.snippets,
     required this.connectSnippetId,
     required this.timeoutValidator,
@@ -313,6 +315,7 @@ class HostAdvancedSection extends StatelessWidget {
     required this.onPredictiveEchoChanged,
     required this.onStartTmuxOnConnectChanged,
     required this.onTmuxPrefixKeyChanged,
+    required this.onUploadCleanupDaysChanged,
     required this.onSnippetsChanged,
     required this.onConnectSnippetChanged,
     super.key,
@@ -326,10 +329,12 @@ class HostAdvancedSection extends StatelessWidget {
   final TextEditingController moshPortsController;
   final TextEditingController tmuxSessionNameController;
   final TextEditingController tmuxStartDirectoryController;
+  final TextEditingController uploadDirectoryController;
   final bool useMosh;
   final bool predictiveEchoEnabled;
   final bool startTmuxOnConnect;
   final TmuxPrefixKey tmuxPrefixKey;
+  final int? uploadCleanupDays;
   final List<TerminalSnippet> snippets;
   final String connectSnippetId;
   final FormFieldValidator<String> timeoutValidator;
@@ -340,6 +345,7 @@ class HostAdvancedSection extends StatelessWidget {
   final ValueChanged<bool> onPredictiveEchoChanged;
   final ValueChanged<bool> onStartTmuxOnConnectChanged;
   final ValueChanged<TmuxPrefixKey> onTmuxPrefixKeyChanged;
+  final ValueChanged<int?> onUploadCleanupDaysChanged;
   final ValueChanged<List<TerminalSnippet>> onSnippetsChanged;
   final ValueChanged<String> onConnectSnippetChanged;
 
@@ -494,6 +500,41 @@ class HostAdvancedSection extends StatelessWidget {
             }
           },
         ),
+        const SizedBox(height: 16),
+        TextFormField(
+          controller: uploadDirectoryController,
+          decoration: const InputDecoration(
+            labelText: 'Upload directory',
+            hintText: '~/.conduit/uploads',
+            helperText:
+                'Where the key-row Upload key stores phone files. Empty uses '
+                '~/.conduit/uploads with one folder per day.',
+            helperMaxLines: 3,
+            prefixIcon: Icon(Icons.drive_folder_upload_outlined),
+          ),
+          autocorrect: false,
+          enableSuggestions: false,
+          textInputAction: TextInputAction.next,
+        ),
+        const SizedBox(height: 12),
+        DropdownButtonFormField<int?>(
+          initialValue: uploadCleanupDays,
+          decoration: const InputDecoration(
+            labelText: 'Delete my uploads after',
+            helperText:
+                'Only files Conduit itself uploaded are ever deleted, on the '
+                'next upload to this machine.',
+            helperMaxLines: 3,
+            prefixIcon: Icon(Icons.auto_delete_outlined),
+          ),
+          items: const [
+            DropdownMenuItem<int?>(child: Text('Never')),
+            DropdownMenuItem<int?>(value: 7, child: Text('7 days')),
+            DropdownMenuItem<int?>(value: 30, child: Text('30 days')),
+            DropdownMenuItem<int?>(value: 90, child: Text('90 days')),
+          ],
+          onChanged: onUploadCleanupDaysChanged,
+        ),
         const SizedBox(height: 18),
         SnippetListEditor(
           title: 'Host snippets',
diff --git a/lib/features/sftp/data/secure_upload_manifest_repository.dart b/lib/features/sftp/data/secure_upload_manifest_repository.dart
new file mode 100644
index 0000000..86cd189
--- /dev/null
+++ b/lib/features/sftp/data/secure_upload_manifest_repository.dart
@@ -0,0 +1,70 @@
+import 'dart:convert';
+
+import 'package:conduit/features/sftp/domain/upload_manifest.dart';
+import 'package:flutter_secure_storage/flutter_secure_storage.dart';
+
+/// Stores the per-host upload manifest as one JSON map
+/// (`hostId -> [{path, at}]`) in secure storage. Corrupt payloads load as
+/// an empty manifest; removing a host's last entry drops the host key.
+class SecureUploadManifestRepository implements UploadManifestRepository {
+  const SecureUploadManifestRepository(this._storage);
+
+  static const _key = 'conduit.upload_manifest.v1';
+
+  final FlutterSecureStorage _storage;
+
+  @override
+  Future<List<UploadManifestEntry>> entriesFor(String hostId) async {
+    final all = await _loadAll();
+    return all[hostId] ?? const [];
+  }
+
+  @override
+  Future<void> setEntries(
+    String hostId,
+    List<UploadManifestEntry> entries,
+  ) async {
+    final all = await _loadAll();
+    if (entries.isEmpty) {
+      all.remove(hostId);
+    } else {
+      all[hostId] = List.of(entries);
+    }
+    await _storage.write(
+      key: _key,
+      value: jsonEncode({
+        for (final MapEntry(:key, :value) in all.entries)
+          key: [for (final entry in value) entry.toJson()],
+      }),
+    );
+  }
+
+  Future<Map<String, List<UploadManifestEntry>>> _loadAll() async {
+    final raw = await _storage.read(key: _key);
+    if (raw == null || raw.trim().isEmpty) {
+      return {};
+    }
+    try {
+      final decoded = jsonDecode(raw);
+      if (decoded is! Map) {
+        return {};
+      }
+      final result = <String, List<UploadManifestEntry>>{};
+      for (final MapEntry(:key, :value) in decoded.entries) {
+        if (key is! String || value is! List) {
+          continue;
+        }
+        final entries = value
+            .map(UploadManifestEntry.fromJson)
+            .whereType<UploadManifestEntry>()
+            .toList();
+        if (entries.isNotEmpty) {
+          result[key] = entries;
+        }
+      }
+      return result;
+    } catch (_) {
+      return {};
+    }
+  }
+}
diff --git a/lib/features/sftp/domain/upload_manifest.dart b/lib/features/sftp/domain/upload_manifest.dart
new file mode 100644
index 0000000..16698a0
--- /dev/null
+++ b/lib/features/sftp/domain/upload_manifest.dart
@@ -0,0 +1,44 @@
+/// A record of one file Conduit uploaded to a host, used so automatic
+/// cleanup can only ever touch files the app itself wrote.
+class UploadManifestEntry {
+  const UploadManifestEntry({required this.path, required this.uploadedAt});
+
+  final String path;
+  final DateTime uploadedAt;
+
+  Map<String, Object?> toJson() {
+    return {'path': path, 'at': uploadedAt.toUtc().millisecondsSinceEpoch};
+  }
+
+  static UploadManifestEntry? fromJson(Object? json) {
+    if (json is! Map) {
+      return null;
+    }
+    final path = json['path'];
+    final at = json['at'];
+    if (path is! String || path.isEmpty || at is! int) {
+      return null;
+    }
+    return UploadManifestEntry(
+      path: path,
+      uploadedAt: DateTime.fromMillisecondsSinceEpoch(at, isUtc: true),
+    );
+  }
+
+  @override
+  bool operator ==(Object other) {
+    return other is UploadManifestEntry &&
+        other.path == path &&
+        other.uploadedAt == uploadedAt;
+  }
+
+  @override
+  int get hashCode => Object.hash(path, uploadedAt);
+}
+
+/// Per-host ledger of Conduit-owned remote uploads.
+abstract class UploadManifestRepository {
+  Future<List<UploadManifestEntry>> entriesFor(String hostId);
+
+  Future<void> setEntries(String hostId, List<UploadManifestEntry> entries);
+}
diff --git a/lib/features/sftp/domain/upload_path.dart b/lib/features/sftp/domain/upload_path.dart
new file mode 100644
index 0000000..4fc1dab
--- /dev/null
+++ b/lib/features/sftp/domain/upload_path.dart
@@ -0,0 +1,99 @@
+/// Pure helpers for building safe remote upload paths.
+library;
+
+/// Default remote directory (under the user's home) that uploads land in,
+/// with one dated subdirectory per day.
+const defaultUploadDirectoryName = '.conduit/uploads';
+
+/// Formats the dated subdirectory for an upload batch: `yyyy-mm-dd`.
+String uploadDateDirectory(DateTime now) {
+  String pad(int value) => value.toString().padLeft(2, '0');
+  return '${now.year.toString().padLeft(4, '0')}-'
+      '${pad(now.month)}-${pad(now.day)}';
+}
+
+/// Resolves the absolute remote upload directory for a host.
+///
+/// [home] is the server-resolved home directory. A [custom] directory from
+/// host settings may be absolute, `~/`-relative, or home-relative; when
+/// absent, uploads go to `$home/.conduit/uploads/<yyyy-mm-dd>`.
+String resolveUploadDirectory({
+  required String home,
+  required DateTime now,
+  String? custom,
+}) {
+  final base = custom?.trim();
+  final root = home.endsWith('/') ? home.substring(0, home.length - 1) : home;
+  if (base == null || base.isEmpty) {
+    return '$root/$defaultUploadDirectoryName/${uploadDateDirectory(now)}';
+  }
+  if (base.startsWith('/')) {
+    return _stripTrailingSlash(base);
+  }
+  if (base == '~') {
+    return root;
+  }
+  if (base.startsWith('~/')) {
+    return _stripTrailingSlash('$root/${base.substring(2)}');
+  }
+  return _stripTrailingSlash('$root/$base');
+}
+
+String _stripTrailingSlash(String path) {
+  return path.length > 1 && path.endsWith('/')
+      ? path.substring(0, path.length - 1)
+      : path;
+}
+
+/// Makes a picked filename safe to use as a single remote path segment.
+///
+/// Path separators and control characters are removed so a hostile or odd
+/// filename cannot escape the upload directory; everything else — spaces,
+/// Unicode, punctuation — is preserved for recognizability because inserted
+/// paths are always shell-quoted separately.
+String sanitizeUploadFileName(String name) {
+  var base = name.split('/').last.split(r'\').last;
+  base = base.replaceAll(RegExp(r'[\x00-\x1f\x7f]'), '').trim();
+  if (base.isEmpty || base == '.' || base == '..') {
+    return 'file';
+  }
+  return base;
+}
+
+/// Picks a name that does not collide with [existing] entries, preserving
+/// the extension: `photo.jpg` becomes `photo-143502.jpg` (upload time), and
+/// `photo-143502-2.jpg` if even that is taken.
+String resolveUploadCollision(String name, Set<String> existing, DateTime now) {
+  if (!existing.contains(name)) {
+    return name;
+  }
+  final dot = name.lastIndexOf('.');
+  final stem = dot > 0 ? name.substring(0, dot) : name;
+  final extension = dot > 0 ? name.substring(dot) : '';
+  String pad(int value) => value.toString().padLeft(2, '0');
+  final stamp = '${pad(now.hour)}${pad(now.minute)}${pad(now.second)}';
+  var candidate = '$stem-$stamp$extension';
+  var counter = 2;
+  while (existing.contains(candidate)) {
+    candidate = '$stem-$stamp-$counter$extension';
+    counter += 1;
+  }
+  return candidate;
+}
+
+const _posixSafePattern = r'^[A-Za-z0-9._/\-]+$';
+
+/// Quotes [value] for safe literal use in a POSIX shell command line.
+///
+/// Values made only of unambiguously safe characters pass through unquoted;
+/// everything else is wrapped in single quotes with embedded single quotes
+/// escaped as `'\''`, which keeps spaces, quotes, `$`, parentheses, newlines,
+/// and globs literal in sh/bash/zsh/fish.
+String posixShellQuote(String value) {
+  if (value.isNotEmpty &&
+      !value.startsWith('-') &&
+      RegExp(_posixSafePattern).hasMatch(value)) {
+    return value;
+  }
+  return "'${value.replaceAll("'", "'\\''")}'";
+}
diff --git a/lib/features/terminal/presentation/terminal_keyboard_bar.dart b/lib/features/terminal/presentation/terminal_keyboard_bar.dart
index a44f0ea..80393dd 100644
--- a/lib/features/terminal/presentation/terminal_keyboard_bar.dart
+++ b/lib/features/terminal/presentation/terminal_keyboard_bar.dart
@@ -23,6 +23,7 @@ class TerminalKeyboardBar extends StatelessWidget {
     required this.onToggleFullscreen,
     this.composeActive = false,
     this.onToggleCompose,
+    this.onUpload,
     required this.onEnterTmuxScrollMode,
     required this.onExitTmuxScrollMode,
     required this.tmuxPrefixKey,
@@ -40,6 +41,9 @@ class TerminalKeyboardBar extends StatelessWidget {
   final VoidCallback onToggleFullscreen;
   final bool composeActive;
   final VoidCallback? onToggleCompose;
+
+  /// Starts the phone-file upload flow for the active session.
+  final VoidCallback? onUpload;
   final VoidCallback onEnterTmuxScrollMode;
   final VoidCallback onExitTmuxScrollMode;
   final TmuxPrefixKey tmuxPrefixKey;
@@ -232,6 +236,12 @@ class TerminalKeyboardBar extends StatelessWidget {
         onSelected: _triggerSnippetMenuItem,
         items: _snippetMenuItems(),
       ),
+      TerminalKeyboardAction.upload => _Key(
+        icon: Icons.upload_file_rounded,
+        palette: palette,
+        brightness: brightness,
+        onPressed: onUpload == null ? null : () => onUpload!(),
+      ),
       _ => _Key(
         label: action.label,
         palette: palette,
@@ -286,6 +296,7 @@ class TerminalKeyboardBar extends StatelessWidget {
       case TerminalKeyboardAction.tmuxMenu:
       case TerminalKeyboardAction.snippets:
       case TerminalKeyboardAction.compose:
+      case TerminalKeyboardAction.upload:
         break;
     }
   }
diff --git a/lib/features/terminal/presentation/terminal_page.dart b/lib/features/terminal/presentation/terminal_page.dart
index 5a0912f..6021aa8 100644
--- a/lib/features/terminal/presentation/terminal_page.dart
+++ b/lib/features/terminal/presentation/terminal_page.dart
@@ -5,30 +5,47 @@ import 'package:conduit/core/presentation/system_navigation_insets.dart';
 import 'package:conduit/core/theme/app_palette.dart';
 import 'package:conduit/core/theme/terminal_appearance.dart';
 import 'package:conduit/core/theme/theme_controller.dart';
+import 'package:conduit/features/sftp/domain/sftp_repository.dart';
+import 'package:conduit/features/sftp/domain/upload_manifest.dart';
+import 'package:conduit/features/sftp/presentation/sftp_browser_controller.dart'
+    show SftpUploadFile;
 import 'package:conduit/features/terminal/domain/security_key_interaction.dart';
 import 'package:conduit/features/terminal/presentation/security_key_picker_dialog.dart';
 import 'package:conduit/features/terminal/presentation/security_key_pin_dialog.dart';
 import 'package:conduit/features/terminal/presentation/terminal_keyboard_bar.dart';
 import 'package:conduit/features/terminal/presentation/terminal_session_controller.dart';
+import 'package:conduit/features/terminal/presentation/terminal_upload_controller.dart';
 import 'package:conduit/features/terminal/presentation/terminal_workspace_controller.dart';
 import 'package:conduit/features/terminal/presentation/widgets/empty_terminal_state.dart';
 import 'package:conduit/features/terminal/presentation/widgets/session_tabs.dart';
 import 'package:conduit/features/terminal/presentation/widgets/terminal_header.dart';
 import 'package:conduit/features/terminal/presentation/widgets/terminal_surface.dart';
+import 'package:conduit/features/terminal/presentation/widgets/terminal_upload_sheet.dart';
 import 'package:conduit_vt/conduit_vt.dart';
+import 'package:file_picker/file_picker.dart';
 import 'package:flutter/material.dart';
 import 'package:flutter/services.dart';
 import 'package:wakelock_plus/wakelock_plus.dart';
 
+/// Picks local files for upload; injectable so tests can avoid the native
+/// file picker. Returns null when the user cancels.
+typedef TerminalUploadFilePicker = Future<List<SftpUploadFile>?> Function();
+
 class TerminalPage extends StatefulWidget {
   const TerminalPage({
     required this.workspace,
     required this.themeController,
+    required this.sftpRepository,
+    required this.uploadManifestRepository,
+    this.uploadFilePicker,
     super.key,
   });
 
   final TerminalWorkspaceController workspace;
   final ThemeController themeController;
+  final SftpRepository sftpRepository;
+  final UploadManifestRepository uploadManifestRepository;
+  final TerminalUploadFilePicker? uploadFilePicker;
 
   @override
   State<TerminalPage> createState() => _TerminalPageState();
@@ -108,6 +125,84 @@ class _TerminalPageState extends State<TerminalPage> {
     _setSystemUiFullscreen(_fullscreen);
   }
 
+  Future<List<SftpUploadFile>?> _pickUploadFiles() async {
+    final custom = widget.uploadFilePicker;
+    if (custom != null) {
+      return custom();
+    }
+    final FilePickerResult? result = await FilePicker.pickFiles(
+      allowMultiple: true,
+      withReadStream: true,
+    );
+    if (result == null || result.files.isEmpty) {
+      return null;
+    }
+    final files = <SftpUploadFile>[];
+    for (final file in result.files) {
+      final readStream = file.readStream;
+      final path = file.path;
+      if (readStream == null && path == null) {
+        continue;
+      }
+      files.add(
+        readStream == null
+            ? SftpUploadFile.local(
+                localPath: path!,
+                name: file.name,
+                size: file.size,
+              )
+            : SftpUploadFile(
+                source: () => readStream,
+                name: file.name,
+                size: file.size,
+              ),
+      );
+    }
+    return files;
+  }
+
+  Future<void> _openUploadFlow(TerminalSessionController session) async {
+    if (session.host.isLocal) {
+      ScaffoldMessenger.of(context).showSnackBar(
+        const SnackBar(
+          content: Text(
+            'Uploads need an SSH machine; the local shell has '
+            'no SFTP endpoint.',
+          ),
+        ),
+      );
+      return;
+    }
+    final List<SftpUploadFile>? files;
+    try {
+      files = await _pickUploadFiles();
+    } catch (error) {
+      if (mounted) {
+        ScaffoldMessenger.of(context).showSnackBar(
+          const SnackBar(content: Text('Could not read the selected files.')),
+        );
+      }
+      return;
+    }
+    if (files == null || files.isEmpty || !mounted) {
+      return;
+    }
+    final controller = TerminalUploadController(
+      host: session.host,
+      repository: widget.sftpRepository,
+      manifest: widget.uploadManifestRepository,
+    );
+    controller.prepare(files);
+    await showTerminalUploadSheet(
+      context: context,
+      controller: controller,
+      // Insert without submitting so the user can add text around the paths.
+      onInsert: session.sendText,
+    );
+    controller.dispose();
+    _focusNode.requestFocus();
+  }
+
   void _setSystemUiFullscreen(bool fullscreen) {
     SystemChrome.setEnabledSystemUIMode(
       fullscreen ? SystemUiMode.immersiveSticky : SystemUiMode.edgeToEdge,
@@ -265,6 +360,8 @@ class _TerminalPageState extends State<TerminalPage> {
                         composeActive: _composeMode,
                         onToggleCompose: () =>
                             setState(() => _composeMode = !_composeMode),
+                        onUpload: () =>
+                            unawaited(_openUploadFlow(activeSession)),
                         tmuxPrefixKey: activeSession.host.tmuxPrefixKey,
                         tmuxScrollMode: _tmuxScrollMode,
                         onEnterTmuxScrollMode: () {
diff --git a/lib/features/terminal/presentation/terminal_upload_controller.dart b/lib/features/terminal/presentation/terminal_upload_controller.dart
new file mode 100644
index 0000000..ab605e3
--- /dev/null
+++ b/lib/features/terminal/presentation/terminal_upload_controller.dart
@@ -0,0 +1,288 @@
+// ignore_for_file: prefer_initializing_formals
+
+import 'dart:async';
+
+import 'package:conduit/features/hosts/domain/saved_host.dart';
+import 'package:conduit/features/sftp/domain/sftp_entry.dart';
+import 'package:conduit/features/sftp/domain/sftp_repository.dart';
+import 'package:conduit/features/sftp/domain/sftp_session.dart';
+import 'package:conduit/features/sftp/domain/upload_manifest.dart';
+import 'package:conduit/features/sftp/domain/upload_path.dart';
+import 'package:conduit/features/sftp/presentation/sftp_browser_controller.dart'
+    show SftpUploadFile;
+import 'package:flutter/foundation.dart';
+
+enum TerminalUploadPhase {
+  confirming,
+  connecting,
+  uploading,
+  success,
+  failed,
+  cancelled,
+}
+
+/// Progress and result for one file within an upload batch.
+class TerminalUploadItem {
+  TerminalUploadItem(this.file);
+
+  final SftpUploadFile file;
+  String? remotePath;
+  int bytesSent = 0;
+  bool done = false;
+
+  double? get fraction {
+    if (file.size <= 0) {
+      return done ? 1 : null;
+    }
+    return (bytesSent / file.size).clamp(0.0, 1.0);
+  }
+}
+
+/// Uploads one batch of picked phone files to a host over SFTP.
+///
+/// Owns a dedicated SFTP session for the batch (opened lazily, always closed
+/// when the batch ends), builds the app-managed remote directory, avoids
+/// name collisions, records every written file in the per-host upload
+/// manifest, and — when the host opts into cleanup — deletes only
+/// manifest-listed files older than the configured age. Nothing outside the
+/// manifest is ever deleted, and directories are never removed.
+class TerminalUploadController extends ChangeNotifier {
+  TerminalUploadController({
+    required this.host,
+    required SftpRepository repository,
+    required UploadManifestRepository manifest,
+    DateTime Function()? now,
+  }) : _repository = repository,
+       _manifest = manifest,
+       _now = now ?? DateTime.now;
+
+  final SavedHost host;
+  final SftpRepository _repository;
+  final UploadManifestRepository _manifest;
+  final DateTime Function() _now;
+
+  TerminalUploadPhase _phase = TerminalUploadPhase.confirming;
+  List<TerminalUploadItem> _items = const [];
+  String? _destination;
+  String? _error;
+  SftpSession? _session;
+  bool _cancelRequested = false;
+  bool _disposed = false;
+
+  TerminalUploadPhase get phase => _phase;
+  List<TerminalUploadItem> get items => List.unmodifiable(_items);
+  String? get destination => _destination;
+  String? get error => _error;
+
+  /// Remote paths of the files that finished uploading.
+  List<String> get uploadedPaths => [
+    for (final item in _items)
+      if (item.done && item.remotePath != null) item.remotePath!,
+  ];
+
+  /// The uploaded paths, individually shell-quoted and space-separated,
+  /// ready to insert into a terminal command line.
+  String get quotedPathsForInsertion =>
+      uploadedPaths.map(posixShellQuote).join(' ');
+
+  void prepare(List<SftpUploadFile> files) {
+    _items = [for (final file in files) TerminalUploadItem(file)];
+    _phase = TerminalUploadPhase.confirming;
+    _error = null;
+    _notify();
+  }
+
+  /// Requests cancellation of an in-flight batch. The session is closed so
+  /// the active transfer aborts promptly instead of draining.
+  Future<void> cancel() async {
+    if (_phase != TerminalUploadPhase.uploading &&
+        _phase != TerminalUploadPhase.connecting) {
+      return;
+    }
+    _cancelRequested = true;
+    final session = _session;
+    _session = null;
+    if (session != null) {
+      try {
+        await session.close();
+      } catch (_) {
+        // The session may already be broken; cancellation still applies.
+      }
+    }
+  }
+
+  Future<void> uploadAll() async {
+    if (_phase == TerminalUploadPhase.uploading ||
+        _phase == TerminalUploadPhase.connecting ||
+        _items.isEmpty) {
+      return;
+    }
+    _cancelRequested = false;
+    _error = null;
+    _phase = TerminalUploadPhase.connecting;
+    _notify();
+    SftpSession? session;
+    // Every file written to the server this batch, persisted to the
+    // manifest in the finally block so partial batches (failure or cancel
+    // mid-write) never leave unrecorded app-owned files behind.
+    final newEntries = <UploadManifestEntry>[];
+    try {
+      session = await _repository.connect(host);
+      _session = session;
+      if (_cancelRequested) {
+        _phase = TerminalUploadPhase.cancelled;
+        _notify();
+        return;
+      }
+      final home = await session.resolve('.');
+      final directory = resolveUploadDirectory(
+        home: home,
+        now: _now(),
+        custom: host.uploadDirectory,
+      );
+      _destination = directory;
+      await _ensureDirectory(session, directory);
+      final existing = <String>{
+        for (final entry in await session.list(directory)) entry.name,
+      };
+      _phase = TerminalUploadPhase.uploading;
+      _notify();
+
+      for (final item in _items) {
+        if (_cancelRequested) {
+          break;
+        }
+        final name = resolveUploadCollision(
+          sanitizeUploadFileName(item.file.name),
+          existing,
+          _now(),
+        );
+        existing.add(name);
+        final remotePath = '$directory/$name';
+        await session.write(
+          remotePath,
+          item.file.openRead(),
+          item.file.size,
+          onProgress: (bytesSent) {
+            item.bytesSent = bytesSent;
+            _notify();
+          },
+        );
+        item.remotePath = remotePath;
+        item.done = true;
+        newEntries.add(
+          UploadManifestEntry(path: remotePath, uploadedAt: _now().toUtc()),
+        );
+        _notify();
+      }
+
+      if (_cancelRequested) {
+        _phase = TerminalUploadPhase.cancelled;
+      } else {
+        // Cleanup of expired earlier uploads only runs after a fully
+        // successful batch; a cancelled or failed batch never deletes.
+        await _cleanUpExpired(session);
+        _phase = TerminalUploadPhase.success;
+      }
+      _notify();
+    } catch (error) {
+      if (_cancelRequested) {
+        _phase = TerminalUploadPhase.cancelled;
+      } else {
+        _phase = TerminalUploadPhase.failed;
+        _error = error.toString();
+      }
+      _notify();
+    } finally {
+      // Record everything that reached the server, even after a failure or
+      // cancellation, so cleanup stays able to manage these files later.
+      if (newEntries.isNotEmpty) {
+        try {
+          await _manifest.setEntries(host.id, [
+            ...await _manifest.entriesFor(host.id),
+            ...newEntries,
+          ]);
+        } catch (_) {
+          // Manifest recording is best-effort; the upload result stands.
+        }
+      }
+      final open = _session;
+      _session = null;
+      if (open != null) {
+        try {
+          await open.close();
+        } catch (_) {
+          // Closing a torn-down session is best-effort.
+        }
+      }
+    }
+  }
+
+  /// Creates the target directory (and its parents) if missing. Individual
+  /// mkdir failures are tolerated — components usually already exist — and
+  /// the directory is verified afterwards by listing it.
+  Future<void> _ensureDirectory(SftpSession session, String directory) async {
+    final segments = directory.split('/').where((s) => s.isNotEmpty).toList();
+    var path = '';
+    for (final segment in segments) {
+      path = '$path/$segment';
+      try {
+        await session.makeDirectory(path);
+      } catch (_) {
+        // Most likely "already exists"; a real failure surfaces below.
+      }
+    }
+  }
+
+  /// Deletes manifest-listed files older than the host's cleanup cutoff and
+  /// drops them from the manifest. Only ever touches exact paths this app
+  /// recorded; never directories.
+  Future<void> _cleanUpExpired(SftpSession session) async {
+    final days = host.uploadCleanupDays;
+    if (days == null || days <= 0) {
+      return;
+    }
+    final entries = await _manifest.entriesFor(host.id);
+    if (entries.isEmpty) {
+      return;
+    }
+    final cutoff = _now().toUtc().subtract(Duration(days: days));
+    final kept = <UploadManifestEntry>[];
+    for (final entry in entries) {
+      if (entry.uploadedAt.isAfter(cutoff)) {
+        kept.add(entry);
+        continue;
+      }
+      try {
+        await session.delete(
+          SftpEntry(
+            name: entry.path.split('/').last,
+            path: entry.path,
+            kind: SftpEntryKind.file,
+          ),
+        );
+      } catch (_) {
+        // Already gone or not deletable; either way the entry is dropped
+        // so a broken file cannot be retried forever.
+      }
+    }
+    await _manifest.setEntries(host.id, kept);
+  }
+
+  void _notify() {
+    if (!_disposed) {
+      notifyListeners();
+    }
+  }
+
+  @override
+  void dispose() {
+    _disposed = true;
+    final open = _session;
+    _session = null;
+    if (open != null) {
+      unawaited(open.close().catchError((_) {}));
+    }
+    super.dispose();
+  }
+}
diff --git a/lib/features/terminal/presentation/widgets/terminal_upload_sheet.dart b/lib/features/terminal/presentation/widgets/terminal_upload_sheet.dart
new file mode 100644
index 0000000..59add99
--- /dev/null
+++ b/lib/features/terminal/presentation/widgets/terminal_upload_sheet.dart
@@ -0,0 +1,242 @@
+import 'package:conduit/features/terminal/presentation/terminal_upload_controller.dart';
+import 'package:flutter/material.dart';
+import 'package:flutter/services.dart';
+
+/// Formats a byte count for display: `532 B`, `1.4 MB`, `2.1 GB`.
+String formatUploadSize(int bytes) {
+  if (bytes < 1024) {
+    return '$bytes B';
+  }
+  const units = ['KB', 'MB', 'GB', 'TB'];
+  var value = bytes.toDouble();
+  var unit = -1;
+  while (value >= 1024 && unit < units.length - 1) {
+    value /= 1024;
+    unit += 1;
+  }
+  return '${value.toStringAsFixed(value >= 100 ? 0 : 1)} ${units[unit]}';
+}
+
+/// Shows the confirm → progress → result flow for one upload batch.
+///
+/// The sheet drives [controller]; nothing uploads until the user confirms.
+/// On success the user can insert the shell-quoted remote paths into the
+/// terminal ([onInsert]) or copy them to the clipboard.
+Future<void> showTerminalUploadSheet({
+  required BuildContext context,
+  required TerminalUploadController controller,
+  required ValueChanged<String> onInsert,
+}) {
+  return showModalBottomSheet<void>(
+    context: context,
+    isScrollControlled: true,
+    useSafeArea: true,
+    isDismissible: false,
+    enableDrag: false,
+    builder: (context) =>
+        TerminalUploadSheet(controller: controller, onInsert: onInsert),
+  );
+}
+
+class TerminalUploadSheet extends StatelessWidget {
+  const TerminalUploadSheet({
+    required this.controller,
+    required this.onInsert,
+    super.key,
+  });
+
+  final TerminalUploadController controller;
+  final ValueChanged<String> onInsert;
+
+  @override
+  Widget build(BuildContext context) {
+    final theme = Theme.of(context);
+    return ListenableBuilder(
+      listenable: controller,
+      builder: (context, _) {
+        return Padding(
+          padding: const EdgeInsets.fromLTRB(16, 12, 16, 16),
+          child: Column(
+            mainAxisSize: MainAxisSize.min,
+            crossAxisAlignment: CrossAxisAlignment.stretch,
+            children: [
+              Text(_title, style: theme.textTheme.titleMedium),
+              const SizedBox(height: 8),
+              if (controller.destination != null) ...[
+                Text(
+                  controller.destination!,
+                  style: theme.textTheme.bodySmall?.copyWith(
+                    fontFamily: 'monospace',
+                  ),
+                ),
+                const SizedBox(height: 8),
+              ],
+              Flexible(
+                child: ListView(
+                  shrinkWrap: true,
+                  children: [
+                    for (final item in controller.items)
+                      _UploadItemTile(item: item, phase: controller.phase),
+                  ],
+                ),
+              ),
+              if (controller.phase == TerminalUploadPhase.failed) ...[
+                const SizedBox(height: 8),
+                Text(
+                  'Upload failed. Nothing was inserted; already-uploaded '
+                  'files stay on the server.',
+                  style: theme.textTheme.bodySmall?.copyWith(
+                    color: theme.colorScheme.error,
+                  ),
+                ),
+              ],
+              const SizedBox(height: 12),
+              _buildActions(context),
+            ],
+          ),
+        );
+      },
+    );
+  }
+
+  String get _title {
+    return switch (controller.phase) {
+      TerminalUploadPhase.confirming => 'Upload to server',
+      TerminalUploadPhase.connecting => 'Connecting…',
+      TerminalUploadPhase.uploading => 'Uploading…',
+      TerminalUploadPhase.success => 'Uploaded',
+      TerminalUploadPhase.failed => 'Upload failed',
+      TerminalUploadPhase.cancelled => 'Upload cancelled',
+    };
+  }
+
+  Widget _buildActions(BuildContext context) {
+    switch (controller.phase) {
+      case TerminalUploadPhase.confirming:
+        return Row(
+          children: [
+            TextButton(
+              onPressed: () => Navigator.of(context).pop(),
+              child: const Text('Cancel'),
+            ),
+            const Spacer(),
+            FilledButton.icon(
+              onPressed: controller.uploadAll,
+              icon: const Icon(Icons.upload_rounded),
+              label: const Text('Upload'),
+            ),
+          ],
+        );
+      case TerminalUploadPhase.connecting:
+      case TerminalUploadPhase.uploading:
+        return Row(
+          children: [
+            const Spacer(),
+            TextButton(
+              onPressed: controller.cancel,
+              child: const Text('Cancel'),
+            ),
+          ],
+        );
+      case TerminalUploadPhase.success:
+      case TerminalUploadPhase.cancelled:
+      case TerminalUploadPhase.failed:
+        final paths = controller.quotedPathsForInsertion;
+        return Row(
+          children: [
+            TextButton(
+              onPressed: () => Navigator.of(context).pop(),
+              child: const Text('Close'),
+            ),
+            const Spacer(),
+            if (paths.isNotEmpty) ...[
+              IconButton(
+                tooltip: 'Copy paths',
+                icon: const Icon(Icons.copy_rounded),
+                onPressed: () {
+                  Clipboard.setData(ClipboardData(text: paths));
+                  ScaffoldMessenger.of(context).showSnackBar(
+                    const SnackBar(content: Text('Remote paths copied.')),
+                  );
+                },
+              ),
+              const SizedBox(width: 6),
+              FilledButton.icon(
+                onPressed: () {
+                  onInsert(paths);
+                  Navigator.of(context).pop();
+                },
+                icon: const Icon(Icons.keyboard_return_rounded),
+                label: const Text('Insert path'),
+              ),
+            ],
+          ],
+        );
+    }
+  }
+}
+
+class _UploadItemTile extends StatelessWidget {
+  const _UploadItemTile({required this.item, required this.phase});
+
+  final TerminalUploadItem item;
+  final TerminalUploadPhase phase;
+
+  @override
+  Widget build(BuildContext context) {
+    final theme = Theme.of(context);
+    final subtitle = item.done
+        ? item.remotePath ?? formatUploadSize(item.file.size)
+        : '${formatUploadSize(item.bytesSent)} of '
+              '${formatUploadSize(item.file.size)}';
+    return Padding(
+      padding: const EdgeInsets.symmetric(vertical: 4),
+      child: Column(
+        crossAxisAlignment: CrossAxisAlignment.stretch,
+        children: [
+          Row(
+            children: [
+              Icon(
+                item.done
+                    ? Icons.check_circle_rounded
+                    : Icons.insert_drive_file_outlined,
+                size: 18,
+                color: item.done
+                    ? theme.colorScheme.primary
+                    : theme.colorScheme.onSurfaceVariant,
+              ),
+              const SizedBox(width: 8),
+              Expanded(
+                child: Text(
+                  item.file.name,
+                  maxLines: 1,
+                  overflow: TextOverflow.ellipsis,
+                ),
+              ),
+              Text(
+                formatUploadSize(item.file.size),
+                style: theme.textTheme.bodySmall,
+              ),
+            ],
+          ),
+          if (phase == TerminalUploadPhase.uploading && !item.done) ...[
+            const SizedBox(height: 4),
+            LinearProgressIndicator(value: item.fraction),
+          ],
+          if (item.done || phase != TerminalUploadPhase.confirming)
+            Padding(
+              padding: const EdgeInsets.only(left: 26, top: 2),
+              child: Text(
+                subtitle,
+                maxLines: 1,
+                overflow: TextOverflow.ellipsis,
+                style: theme.textTheme.bodySmall?.copyWith(
+                  fontFamily: 'monospace',
+                ),
+              ),
+            ),
+        ],
+      ),
+    );
+  }
+}
diff --git a/lib/main.dart b/lib/main.dart
index edec549..983bb20 100644
--- a/lib/main.dart
+++ b/lib/main.dart
@@ -16,8 +16,10 @@ import 'package:conduit/features/local_shell/local_shell_licenses.dart';
 import 'package:conduit/features/local_shell/presentation/local_shell_controller.dart';
 import 'package:conduit/features/sftp/data/dart_ssh_sftp_repository.dart';
 import 'package:conduit/features/sftp/data/file_picker_file_export.dart';
+import 'package:conduit/features/sftp/data/secure_upload_manifest_repository.dart';
 import 'package:conduit/features/sftp/domain/file_export.dart';
 import 'package:conduit/features/sftp/domain/sftp_repository.dart';
+import 'package:conduit/features/sftp/domain/upload_manifest.dart';
 import 'package:conduit/features/terminal/data/connectivity_plus_network.dart';
 import 'package:conduit/features/terminal/data/dart_ssh_terminal_repository.dart';
 import 'package:conduit/features/terminal/data/mosh_terminal_repository.dart';
@@ -64,6 +66,9 @@ void main() {
     ConnectivityPlusNetwork(),
   );
   final sftpRepository = DartSshSftpRepository(hostKeyVerifier);
+  const uploadManifestRepository = SecureUploadManifestRepository(
+    secureStorage,
+  );
   final backupService = AppBackupService(
     hostsController: hostsController,
     themeController: themeController,
@@ -84,6 +89,7 @@ void main() {
       hostKeyVerifier: hostKeyVerifier,
       promptCoordinator: promptCoordinator,
       sftpRepository: sftpRepository,
+      uploadManifestRepository: uploadManifestRepository,
       backupService: backupService,
       fileExport: fileExport,
     ),
@@ -101,6 +107,7 @@ class ConduitApp extends StatefulWidget {
     required this.hostKeyVerifier,
     required this.promptCoordinator,
     required this.sftpRepository,
+    required this.uploadManifestRepository,
     required this.backupService,
     required this.fileExport,
     super.key,
@@ -115,6 +122,7 @@ class ConduitApp extends StatefulWidget {
   final HostKeyVerifier hostKeyVerifier;
   final HostKeyPromptCoordinator promptCoordinator;
   final SftpRepository sftpRepository;
+  final UploadManifestRepository uploadManifestRepository;
   final AppBackupService backupService;
   final FileExport fileExport;
 
@@ -258,6 +266,7 @@ class _ConduitAppState extends State<ConduitApp> with WidgetsBindingObserver {
                 hostKeyVerifier: widget.hostKeyVerifier,
                 promptCoordinator: widget.promptCoordinator,
                 sftpRepository: widget.sftpRepository,
+                uploadManifestRepository: widget.uploadManifestRepository,
                 backupService: widget.backupService,
                 fileExport: widget.fileExport,
               );
diff --git a/pubspec.lock b/pubspec.lock
index dd7c52a..13dcdef 100644
--- a/pubspec.lock
+++ b/pubspec.lock
@@ -800,7 +800,7 @@ packages:
     source: hosted
     version: "1.5.2"
   wakelock_plus_platform_interface:
-    dependency: transitive
+    dependency: "direct dev"
     description:
       name: wakelock_plus_platform_interface
       sha256: b13f99e992e7ae6a152e16c5559d3c07ff445b13330192662494e614ca3e7d7b
diff --git a/pubspec.yaml b/pubspec.yaml
index ea8c5c3..e458c4b 100644
--- a/pubspec.yaml
+++ b/pubspec.yaml
@@ -44,6 +44,7 @@ dev_dependencies:
 
   flutter_lints: ^6.0.0
   flutter_launcher_icons: ^0.14.4
+  wakelock_plus_platform_interface: ^1.5.1
 
 flutter_launcher_icons:
   android: "ic_launcher"
diff --git a/test/core/system_navigation_insets_test.dart b/test/core/system_navigation_insets_test.dart
index 1e25d2e..54d68ce 100644
--- a/test/core/system_navigation_insets_test.dart
+++ b/test/core/system_navigation_insets_test.dart
@@ -83,6 +83,7 @@ void main() {
         hostKeyVerifier: verifier,
         promptCoordinator: promptCoordinator,
         sftpRepository: NoNetworkSftpRepository(),
+        uploadManifestRepository: InMemoryUploadManifest(),
         backupService: AppBackupService(
           hostsController: hostsController,
           themeController: themeController,
@@ -130,6 +131,7 @@ void main() {
         hostKeyVerifier: verifier,
         promptCoordinator: promptCoordinator,
         sftpRepository: NoNetworkSftpRepository(),
+        uploadManifestRepository: InMemoryUploadManifest(),
         backupService: AppBackupService(
           hostsController: hostsController,
           themeController: themeController,
@@ -212,6 +214,8 @@ void main() {
         home: TerminalPage(
           workspace: workspace,
           themeController: themeController,
+          sftpRepository: NoNetworkSftpRepository(),
+          uploadManifestRepository: InMemoryUploadManifest(),
         ),
       ),
     );
diff --git a/test/core/theme_preferences_repository_test.dart b/test/core/theme_preferences_repository_test.dart
index e43a1da..8f0e649 100644
--- a/test/core/theme_preferences_repository_test.dart
+++ b/test/core/theme_preferences_repository_test.dart
@@ -31,6 +31,7 @@ void main() {
             TerminalKeyboardAction.control,
             TerminalKeyboardAction.arrowDown,
             TerminalKeyboardAction.snippets,
+            TerminalKeyboardAction.upload,
           ],
         );
       },
@@ -51,6 +52,7 @@ void main() {
           items: [
             TerminalKeyboardItem.builtIn(TerminalKeyboardAction.escape),
             TerminalKeyboardItem.builtIn(TerminalKeyboardAction.snippets),
+            TerminalKeyboardItem.builtIn(TerminalKeyboardAction.upload),
           ],
         ),
       ]);
diff --git a/test/features/hosts/hosts_test.dart b/test/features/hosts/hosts_test.dart
index ad2eb2c..856b2bb 100644
--- a/test/features/hosts/hosts_test.dart
+++ b/test/features/hosts/hosts_test.dart
@@ -169,6 +169,8 @@ void main() {
           ),
         ],
         connectSnippetId: 'snippet:deploy',
+        uploadDirectory: '~/drops',
+        uploadCleanupDays: 30,
         lastConnectedAt: DateTime.parse('2025-01-02T03:04:05Z'),
       );
 
@@ -198,9 +200,26 @@ void main() {
       expect(decoded.tmuxStartDirectory, original.tmuxStartDirectory);
       expect(decoded.snippets, original.snippets);
       expect(decoded.connectSnippetId, original.connectSnippetId);
+      expect(decoded.uploadDirectory, original.uploadDirectory);
+      expect(decoded.uploadCleanupDays, original.uploadCleanupDays);
       expect(decoded.lastConnectedAt, original.lastConnectedAt);
     });
 
+    test('missing or corrupt upload settings load as defaults', () {
+      final decoded = SavedHost.fromJson(const {
+        'id': 'id',
+        'name': 'n',
+        'host': 'h',
+        'port': 22,
+        'username': 'u',
+        'authMethod': 'password',
+        'uploadCleanupDays': 'soon',
+      });
+
+      expect(decoded.uploadDirectory, '');
+      expect(decoded.uploadCleanupDays, isNull);
+    });
+
     test('invalid persisted mosh ports fall back to the default', () {
       final decoded = SavedHost.fromJson(const {
         'id': 'id',
diff --git a/test/features/sftp/upload_manifest_test.dart b/test/features/sftp/upload_manifest_test.dart
new file mode 100644
index 0000000..5c9427d
--- /dev/null
+++ b/test/features/sftp/upload_manifest_test.dart
@@ -0,0 +1,68 @@
+import 'package:conduit/features/sftp/data/secure_upload_manifest_repository.dart';
+import 'package:conduit/features/sftp/domain/upload_manifest.dart';
+import 'package:flutter_test/flutter_test.dart';
+
+import '../../support/test_doubles.dart';
+
+void main() {
+  group('SecureUploadManifestRepository', () {
+    final entryA = UploadManifestEntry(
+      path: '/home/u/.conduit/uploads/2026-07-04/a.png',
+      uploadedAt: DateTime.utc(2026, 7, 4, 10),
+    );
+    final entryB = UploadManifestEntry(
+      path: '/home/u/.conduit/uploads/2026-07-04/b.pdf',
+      uploadedAt: DateTime.utc(2026, 7, 4, 11),
+    );
+
+    test('round-trips entries per host', () async {
+      final storage = InMemorySecureStorage();
+      final repository = SecureUploadManifestRepository(storage);
+
+      await repository.setEntries('host-1', [entryA]);
+      await repository.setEntries('host-2', [entryB]);
+
+      expect(await repository.entriesFor('host-1'), [entryA]);
+      expect(await repository.entriesFor('host-2'), [entryB]);
+      expect(await repository.entriesFor('host-3'), isEmpty);
+    });
+
+    test('drops a host key when its entries empty out', () async {
+      final storage = InMemorySecureStorage();
+      final repository = SecureUploadManifestRepository(storage);
+
+      await repository.setEntries('host-1', [entryA]);
+      await repository.setEntries('host-1', []);
+
+      expect(await repository.entriesFor('host-1'), isEmpty);
+      final raw = await storage.read(key: 'conduit.upload_manifest.v1');
+      expect(raw, isNot(contains('host-1')));
+    });
+
+    test('loads corrupt payloads as an empty manifest', () async {
+      final storage = InMemorySecureStorage();
+      await storage.write(
+        key: 'conduit.upload_manifest.v1',
+        value: 'not-json{{{',
+      );
+      final repository = SecureUploadManifestRepository(storage);
+
+      expect(await repository.entriesFor('host-1'), isEmpty);
+    });
+
+    test('skips malformed entries while keeping valid ones', () async {
+      final storage = InMemorySecureStorage();
+      await storage.write(
+        key: 'conduit.upload_manifest.v1',
+        value:
+            '{"host-1":[{"path":"/ok","at":1000},{"path":"","at":2},'
+            '{"nope":true},42]}',
+      );
+      final repository = SecureUploadManifestRepository(storage);
+
+      final entries = await repository.entriesFor('host-1');
+      expect(entries, hasLength(1));
+      expect(entries.single.path, '/ok');
+    });
+  });
+}
diff --git a/test/features/sftp/upload_path_test.dart b/test/features/sftp/upload_path_test.dart
new file mode 100644
index 0000000..e3003f1
--- /dev/null
+++ b/test/features/sftp/upload_path_test.dart
@@ -0,0 +1,131 @@
+import 'package:conduit/features/sftp/domain/upload_path.dart';
+import 'package:flutter_test/flutter_test.dart';
+
+void main() {
+  group('resolveUploadDirectory', () {
+    final now = DateTime(2026, 7, 4);
+
+    test('defaults to a dated folder under ~/.conduit/uploads', () {
+      expect(
+        resolveUploadDirectory(home: '/home/user', now: now),
+        '/home/user/.conduit/uploads/2026-07-04',
+      );
+    });
+
+    test('trims a trailing slash from home', () {
+      expect(
+        resolveUploadDirectory(home: '/home/user/', now: now),
+        '/home/user/.conduit/uploads/2026-07-04',
+      );
+    });
+
+    test('accepts absolute, tilde-relative, and home-relative overrides', () {
+      expect(
+        resolveUploadDirectory(home: '/h', now: now, custom: '/srv/drop/'),
+        '/srv/drop',
+      );
+      expect(
+        resolveUploadDirectory(home: '/h', now: now, custom: '~/incoming'),
+        '/h/incoming',
+      );
+      expect(
+        resolveUploadDirectory(home: '/h', now: now, custom: 'incoming'),
+        '/h/incoming',
+      );
+      expect(resolveUploadDirectory(home: '/h', now: now, custom: '~'), '/h');
+    });
+
+    test('treats blank overrides as the default', () {
+      expect(
+        resolveUploadDirectory(home: '/h', now: now, custom: '   '),
+        '/h/.conduit/uploads/2026-07-04',
+      );
+    });
+  });
+
+  group('sanitizeUploadFileName', () {
+    test('keeps ordinary names, spaces, and unicode intact', () {
+      expect(
+        sanitizeUploadFileName('Screenshot 2026.png'),
+        'Screenshot 2026.png',
+      );
+      expect(sanitizeUploadFileName('фото ☕.jpg'), 'фото ☕.jpg');
+    });
+
+    test('strips directory components from path-like names', () {
+      expect(sanitizeUploadFileName('../../etc/passwd'), 'passwd');
+      expect(sanitizeUploadFileName(r'C:\Users\me\doc.pdf'), 'doc.pdf');
+    });
+
+    test('removes control characters', () {
+      expect(sanitizeUploadFileName('bad\x00name\x1f.txt'), 'badname.txt');
+    });
+
+    test('falls back for empty or dot names', () {
+      expect(sanitizeUploadFileName(''), 'file');
+      expect(sanitizeUploadFileName('..'), 'file');
+      expect(sanitizeUploadFileName('  '), 'file');
+    });
+  });
+
+  group('resolveUploadCollision', () {
+    final now = DateTime(2026, 7, 4, 14, 35, 2);
+
+    test('keeps a non-colliding name', () {
+      expect(resolveUploadCollision('a.jpg', {'b.jpg'}, now), 'a.jpg');
+    });
+
+    test('adds a timestamp before the extension on collision', () {
+      expect(
+        resolveUploadCollision('photo.jpg', {'photo.jpg'}, now),
+        'photo-143502.jpg',
+      );
+    });
+
+    test('adds a counter when the timestamped name also collides', () {
+      expect(
+        resolveUploadCollision('photo.jpg', {
+          'photo.jpg',
+          'photo-143502.jpg',
+        }, now),
+        'photo-143502-2.jpg',
+      );
+    });
+
+    test('handles extensionless and dotfile names', () {
+      expect(resolveUploadCollision('notes', {'notes'}, now), 'notes-143502');
+      expect(
+        resolveUploadCollision('.envrc', {'.envrc'}, now),
+        '.envrc-143502',
+      );
+    });
+  });
+
+  group('posixShellQuote', () {
+    test('passes through unambiguously safe values', () {
+      expect(posixShellQuote('/home/user/file.txt'), '/home/user/file.txt');
+      expect(posixShellQuote('a-b_c.1/d'), 'a-b_c.1/d');
+    });
+
+    test('quotes spaces, globs, and metacharacters', () {
+      expect(posixShellQuote('my file.txt'), "'my file.txt'");
+      expect(posixShellQuote(r'a$(rm -rf).txt'), r"'a$(rm -rf).txt'");
+      expect(posixShellQuote('a*b?.txt'), "'a*b?.txt'");
+      expect(posixShellQuote('semi;colon'), "'semi;colon'");
+      expect(posixShellQuote('(parens).pdf'), "'(parens).pdf'");
+    });
+
+    test('escapes embedded single quotes', () {
+      expect(posixShellQuote("it's here.txt"), r"'it'\''s here.txt'");
+    });
+
+    test('quotes newlines and leading dashes', () {
+      expect(posixShellQuote('line\nbreak'), "'line\nbreak'");
+      expect(posixShellQuote('-rf'), "'-rf'");
+    });
+
+    test('quotes the empty string', () {
+      expect(posixShellQuote(''), "''");
+    });
+  });
+}
diff --git a/test/features/terminal/terminal_upload_test.dart b/test/features/terminal/terminal_upload_test.dart
new file mode 100644
index 0000000..916b898
--- /dev/null
+++ b/test/features/terminal/terminal_upload_test.dart
@@ -0,0 +1,449 @@
+import 'dart:convert';
+import 'dart:typed_data';
+
+import 'package:conduit/core/theme/terminal_appearance.dart';
+import 'package:conduit/core/theme/theme_controller.dart';
+import 'package:conduit/features/hosts/domain/saved_host.dart';
+import 'package:conduit/features/sftp/domain/sftp_entry.dart';
+import 'package:conduit/features/sftp/domain/upload_manifest.dart';
+import 'package:conduit/features/sftp/presentation/sftp_browser_controller.dart'
+    show SftpUploadFile;
+import 'package:conduit/features/terminal/presentation/terminal_page.dart';
+import 'package:conduit/features/terminal/presentation/terminal_upload_controller.dart';
+import 'package:conduit/features/terminal/presentation/terminal_workspace_controller.dart';
+import 'package:conduit/features/terminal/presentation/widgets/terminal_upload_sheet.dart';
+import 'package:flutter/material.dart';
+import 'package:flutter_test/flutter_test.dart';
+import 'package:wakelock_plus_platform_interface/wakelock_plus_platform_interface.dart';
+
+import '../../support/test_doubles.dart';
+
+class _NoopWakelock extends WakelockPlusPlatformInterface {
+  @override
+  Future<void> toggle({required bool enable}) async {}
+
+  @override
+  Future<bool> get enabled async => false;
+}
+
+SftpEntry _entryNamed(String name) {
+  return SftpEntry(name: name, path: '/x/$name', kind: SftpEntryKind.file);
+}
+
+SftpUploadFile _file(String name, List<int> bytes) {
+  return SftpUploadFile(
+    source: () => Stream.value(Uint8List.fromList(bytes)),
+    name: name,
+    size: bytes.length,
+  );
+}
+
+void main() {
+  TestWidgetsFlutterBinding.ensureInitialized();
+  WakelockPlusPlatformInterface.instance = _NoopWakelock();
+
+  final fixedNow = DateTime(2026, 7, 4, 14, 35, 2);
+
+  group('TerminalUploadController', () {
+    late FakeSftpSession session;
+    late InMemoryUploadManifest manifest;
+
+    TerminalUploadController buildController({
+      SavedHost? host,
+      Object? writeError,
+    }) {
+      session = FakeSftpSession(
+        home: '/home/u',
+        tree: {'/home/u': []},
+        writeError: writeError,
+      );
+      manifest = InMemoryUploadManifest();
+      return TerminalUploadController(
+        host: host ?? buildHost('h1'),
+        repository: FakeSftpRepository(session),
+        manifest: manifest,
+        now: () => fixedNow,
+      );
+    }
+
+    test(
+      'creates the dated directory chain and uploads with progress',
+      () async {
+        final controller = buildController();
+        final progress = <TerminalUploadPhase>[];
+        controller.addListener(() => progress.add(controller.phase));
+        controller.prepare([
+          _file('photo one.jpg', [1, 2, 3, 4]),
+        ]);
+
+        await controller.uploadAll();
+
+        expect(controller.phase, TerminalUploadPhase.success);
+        expect(session.madeDirectories, [
+          '/home',
+          '/home/u',
+          '/home/u/.conduit',
+          '/home/u/.conduit/uploads',
+          '/home/u/.conduit/uploads/2026-07-04',
+        ]);
+        const path = '/home/u/.conduit/uploads/2026-07-04/photo one.jpg';
+        expect(session.writtenFiles[path], [1, 2, 3, 4]);
+        expect(controller.uploadedPaths, [path]);
+        expect(
+          controller.quotedPathsForInsertion,
+          "'/home/u/.conduit/uploads/2026-07-04/photo one.jpg'",
+        );
+        expect(manifest.entries['h1'], hasLength(1));
+        expect(session.closeCount, 1);
+      },
+    );
+
+    test('sanitizes hostile names and resolves collisions', () async {
+      final controller = buildController();
+      session.tree['/home/u/.conduit/uploads/2026-07-04'] = [
+        _entryNamed('photo.jpg'),
+      ];
+      // Pre-seeding the tree means makeDirectory must not clobber it.
+      controller.prepare([
+        _file('../../photo.jpg', [1]),
+        _file('photo.jpg', [2]),
+      ]);
+
+      await controller.uploadAll();
+
+      expect(controller.phase, TerminalUploadPhase.success);
+      expect(controller.uploadedPaths, [
+        '/home/u/.conduit/uploads/2026-07-04/photo-143502.jpg',
+        '/home/u/.conduit/uploads/2026-07-04/photo-143502-2.jpg',
+      ]);
+    });
+
+    test('uploads to a custom per-host directory', () async {
+      final controller = buildController(
+        host: buildHost('h1').copyWith(uploadDirectory: '~/drop zone'),
+      );
+      controller.prepare([
+        _file('a.txt', [7]),
+      ]);
+
+      await controller.uploadAll();
+
+      expect(controller.uploadedPaths, ['/home/u/drop zone/a.txt']);
+      expect(controller.quotedPathsForInsertion, "'/home/u/drop zone/a.txt'");
+    });
+
+    test(
+      'reports failure and keeps state recoverable on write errors',
+      () async {
+        final controller = buildController(writeError: StateError('disk full'));
+        controller.prepare([
+          _file('a.txt', [1]),
+        ]);
+
+        await controller.uploadAll();
+
+        expect(controller.phase, TerminalUploadPhase.failed);
+        expect(controller.error, contains('disk full'));
+        expect(controller.uploadedPaths, isEmpty);
+        expect(manifest.entries, isEmpty);
+        expect(session.closeCount, 1);
+      },
+    );
+
+    test('records already-uploaded files in the manifest when a later file '
+        'fails', () async {
+      session = FakeSftpSession(
+        home: '/home/u',
+        tree: {'/home/u': []},
+        failWriteAtIndex: 1,
+      );
+      manifest = InMemoryUploadManifest();
+      final controller = TerminalUploadController(
+        host: buildHost('h1'),
+        repository: FakeSftpRepository(session),
+        manifest: manifest,
+        now: () => fixedNow,
+      );
+      controller.prepare([
+        _file('first.txt', [1]),
+        _file('second.txt', [2]),
+      ]);
+
+      await controller.uploadAll();
+
+      expect(controller.phase, TerminalUploadPhase.failed);
+      // The first file reached the server, so cleanup must know about it.
+      expect(manifest.entries['h1']!.map((e) => e.path), [
+        '/home/u/.conduit/uploads/2026-07-04/first.txt',
+      ]);
+      // A failed batch never deletes anything.
+      expect(session.deletedPaths, isEmpty);
+    });
+
+    test('a cancelled batch records uploads but never deletes', () async {
+      final controller = buildController(
+        host: buildHost('h1').copyWith(uploadCleanupDays: 7),
+      );
+      manifest.entries['h1'] = [
+        UploadManifestEntry(
+          path: '/old/expired.png',
+          uploadedAt: DateTime.utc(2020),
+        ),
+      ];
+      controller.prepare([
+        _file('a.txt', [1]),
+        _file('b.txt', [2]),
+      ]);
+      controller.addListener(() {
+        if (controller.items.first.done &&
+            controller.phase == TerminalUploadPhase.uploading) {
+          controller.cancel();
+        }
+      });
+
+      await controller.uploadAll();
+
+      expect(controller.phase, TerminalUploadPhase.cancelled);
+      expect(session.deletedPaths, isEmpty);
+      expect(
+        manifest.entries['h1']!.map((e) => e.path),
+        containsAll([
+          '/old/expired.png',
+          '/home/u/.conduit/uploads/2026-07-04/a.txt',
+        ]),
+      );
+    });
+
+    test('fails cleanly when the connection cannot be opened', () async {
+      final controller = TerminalUploadController(
+        host: buildHost('h1'),
+        repository: ThrowingSftpRepository(),
+        manifest: InMemoryUploadManifest(),
+        now: () => fixedNow,
+      );
+      controller.prepare([
+        _file('a.txt', [1]),
+      ]);
+
+      await controller.uploadAll();
+
+      expect(controller.phase, TerminalUploadPhase.failed);
+      expect(controller.error, isNotNull);
+    });
+
+    test(
+      'cancelling between files stops the batch and closes the session',
+      () async {
+        final controller = buildController();
+        controller.prepare([
+          _file('a.txt', [1]),
+          _file('b.txt', [2]),
+        ]);
+        controller.addListener(() {
+          if (controller.items.first.done &&
+              controller.phase == TerminalUploadPhase.uploading) {
+            controller.cancel();
+          }
+        });
+
+        await controller.uploadAll();
+
+        expect(controller.phase, TerminalUploadPhase.cancelled);
+        expect(controller.uploadedPaths, hasLength(1));
+        expect(session.writtenFiles.keys, hasLength(1));
+        expect(session.closeCount, greaterThanOrEqualTo(1));
+      },
+    );
+
+    test('zero-byte files upload successfully', () async {
+      final controller = buildController();
+      controller.prepare([_file('empty.txt', [])]);
+
+      await controller.uploadAll();
+
+      expect(controller.phase, TerminalUploadPhase.success);
+      expect(
+        session.writtenFiles['/home/u/.conduit/uploads/2026-07-04/empty.txt'],
+        isEmpty,
+      );
+    });
+
+    test(
+      'cleanup deletes only manifest-listed files past the cutoff',
+      () async {
+        final controller = buildController(
+          host: buildHost('h1').copyWith(uploadCleanupDays: 7),
+        );
+        manifest.entries['h1'] = [
+          UploadManifestEntry(
+            path: '/home/u/.conduit/uploads/2026-06-01/old.png',
+            uploadedAt: DateTime.utc(2026, 6),
+          ),
+          UploadManifestEntry(
+            path: '/home/u/.conduit/uploads/2026-07-03/fresh.png',
+            uploadedAt: DateTime.utc(2026, 7, 3),
+          ),
+        ];
+        controller.prepare([
+          _file('new.txt', [1]),
+        ]);
+
+        await controller.uploadAll();
+
+        expect(session.deletedPaths, [
+          '/home/u/.conduit/uploads/2026-06-01/old.png',
+        ]);
+        final kept = manifest.entries['h1']!.map((e) => e.path).toList();
+        expect(
+          kept,
+          isNot(contains('/home/u/.conduit/uploads/2026-06-01/old.png')),
+        );
+        expect(kept, contains('/home/u/.conduit/uploads/2026-07-03/fresh.png'));
+        expect(kept, contains('/home/u/.conduit/uploads/2026-07-04/new.txt'));
+      },
+    );
+
+    test('never deletes when cleanup is disabled', () async {
+      final controller = buildController();
+      manifest.entries['h1'] = [
+        UploadManifestEntry(
+          path: '/somewhere/ancient.png',
+          uploadedAt: DateTime.utc(2020),
+        ),
+      ];
+      controller.prepare([
+        _file('new.txt', [1]),
+      ]);
+
+      await controller.uploadAll();
+
+      expect(session.deletedPaths, isEmpty);
+      expect(
+        manifest.entries['h1']!.map((e) => e.path),
+        contains('/somewhere/ancient.png'),
+      );
+    });
+  });
+
+  group('Terminal upload flow', () {
+    testWidgets('picker → confirm → progress → insert quoted path', (
+      tester,
+    ) async {
+      final terminalSession = TrackableTerminalSession();
+      final workspace = TerminalWorkspaceController(
+        ImmediateTerminalRepository(terminalSession),
+      );
+      final themeController = ThemeController(InMemoryThemePreferences());
+      final sftpSession = FakeSftpSession(
+        home: '/home/u',
+        tree: {'/home/u': []},
+      );
+      final controller = workspace.open(buildHost('h1'));
+      await tester.runAsync(controller.connect);
+      addTearDown(workspace.dispose);
+
+      await tester.pumpWidget(
+        MaterialApp(
+          home: TerminalPage(
+            workspace: workspace,
+            themeController: themeController,
+            sftpRepository: FakeSftpRepository(sftpSession),
+            uploadManifestRepository: InMemoryUploadManifest(),
+            uploadFilePicker: () async => [
+              _file('my shot.png', [9, 9]),
+            ],
+          ),
+        ),
+      );
+      await tester.pump();
+      await themeController.setTerminalKeyboardRows(const [
+        TerminalKeyboardRow(
+          items: [TerminalKeyboardItem.builtIn(TerminalKeyboardAction.upload)],
+        ),
+      ]);
+      await tester.pump();
+
+      await tester.tap(find.byIcon(Icons.upload_file_rounded));
+      await tester.pump();
+      await tester.pump(const Duration(milliseconds: 350));
+
+      // Confirmation state: filename, size, and explicit Upload action.
+      expect(find.byType(TerminalUploadSheet), findsOneWidget);
+      expect(find.text('my shot.png'), findsOneWidget);
+      expect(find.text('2 B'), findsOneWidget);
+      expect(sftpSession.writtenFiles, isEmpty);
+
+      await tester.tap(find.text('Upload'));
+      await tester.pump();
+      await tester.pump();
+      await tester.pump(const Duration(milliseconds: 100));
+
+      expect(find.text('Uploaded'), findsOneWidget);
+      expect(sftpSession.writtenFiles.keys.single, endsWith('/my shot.png'));
+
+      await tester.tap(find.text('Insert path'));
+      await tester.pump();
+      await tester.pump(const Duration(milliseconds: 350));
+
+      expect(find.byType(TerminalUploadSheet), findsNothing);
+      final sent = terminalSession.sent
+          .map((bytes) => utf8.decode(bytes))
+          .join();
+      expect(sent, contains("'"));
+      expect(sent, contains('/my shot.png'));
+      // Inserted, not executed: no Enter was sent.
+      expect(sent, isNot(contains('\r')));
+
+      // Flush the terminal resize debounce timer.
+      await tester.pump(const Duration(milliseconds: 300));
+    });
+
+    testWidgets('failed uploads surface an error state', (tester) async {
+      final workspace = TerminalWorkspaceController(
+        ImmediateTerminalRepository(TrackableTerminalSession()),
+      );
+      final themeController = ThemeController(InMemoryThemePreferences());
+      final controller = workspace.open(buildHost('h1'));
+      await tester.runAsync(controller.connect);
+      addTearDown(workspace.dispose);
+
+      await tester.pumpWidget(
+        MaterialApp(
+          home: TerminalPage(
+            workspace: workspace,
+            themeController: themeController,
+            sftpRepository: ThrowingSftpRepository(),
+            uploadManifestRepository: InMemoryUploadManifest(),
+            uploadFilePicker: () async => [
+              _file('a.txt', [1]),
+            ],
+          ),
+        ),
+      );
+      await tester.pump();
+      await themeController.setTerminalKeyboardRows(const [
+        TerminalKeyboardRow(
+          items: [TerminalKeyboardItem.builtIn(TerminalKeyboardAction.upload)],
+        ),
+      ]);
+      await tester.pump();
+
+      await tester.tap(find.byIcon(Icons.upload_file_rounded));
+      await tester.pump();
+      await tester.pump(const Duration(milliseconds: 350));
+      await tester.tap(find.text('Upload'));
+      await tester.pump();
+      await tester.pump(const Duration(milliseconds: 100));
+
+      expect(find.text('Upload failed'), findsOneWidget);
+      expect(find.textContaining('Nothing was inserted'), findsOneWidget);
+
+      await tester.tap(find.text('Close'));
+      await tester.pump();
+      await tester.pump(const Duration(milliseconds: 350));
+      expect(find.byType(TerminalUploadSheet), findsNothing);
+
+      await tester.pump(const Duration(milliseconds: 300));
+    });
+  });
+}
diff --git a/test/support/test_doubles.dart b/test/support/test_doubles.dart
index 1315a25..67b4259 100644
--- a/test/support/test_doubles.dart
+++ b/test/support/test_doubles.dart
@@ -11,6 +11,7 @@ import 'package:conduit/features/sftp/domain/file_export.dart';
 import 'package:conduit/features/sftp/domain/sftp_entry.dart';
 import 'package:conduit/features/sftp/domain/sftp_repository.dart';
 import 'package:conduit/features/sftp/domain/sftp_session.dart';
+import 'package:conduit/features/sftp/domain/upload_manifest.dart';
 import 'package:conduit/features/terminal/domain/host_key_prompt.dart';
 import 'package:conduit/features/terminal/domain/host_key_verifier.dart';
 import 'package:conduit/features/terminal/domain/network_connectivity.dart';
@@ -426,6 +427,26 @@ class NoopVerifier implements HostKeyVerifier {
   }) async => false;
 }
 
+class InMemoryUploadManifest implements UploadManifestRepository {
+  final Map<String, List<UploadManifestEntry>> entries = {};
+
+  @override
+  Future<List<UploadManifestEntry>> entriesFor(String hostId) async =>
+      List.of(entries[hostId] ?? const []);
+
+  @override
+  Future<void> setEntries(
+    String hostId,
+    List<UploadManifestEntry> newEntries,
+  ) async {
+    if (newEntries.isEmpty) {
+      entries.remove(hostId);
+    } else {
+      entries[hostId] = List.of(newEntries);
+    }
+  }
+}
+
 class NoNetworkSftpRepository implements SftpRepository {
   @override
   Future<SftpSession> connect(SavedHost host) {
@@ -448,13 +469,27 @@ class ThrowingSftpRepository implements SftpRepository {
 }
 
 class FakeSftpSession implements SftpSession {
-  FakeSftpSession({required this.home, required this.tree});
+  FakeSftpSession({
+    required this.home,
+    required this.tree,
+    this.writeError,
+    this.failWriteAtIndex,
+  });
 
   final String home;
   final Map<String, List<SftpEntry>> tree;
   final List<String> madeDirectories = [];
   final Map<String, List<int>> writtenFiles = {};
   final Map<String, int> listCalls = {};
+  final List<String> deletedPaths = [];
+  int closeCount = 0;
+
+  /// When set, every write throws this error after draining nothing.
+  final Object? writeError;
+
+  /// When set, only the write with this zero-based index throws.
+  final int? failWriteAtIndex;
+  int _writeCount = 0;
 
   @override
   Future<List<SftpEntry>> list(String path) async {
@@ -486,6 +521,12 @@ class FakeSftpSession implements SftpSession {
     int length, {
     void Function(int bytesSent)? onProgress,
   }) async {
+    final index = _writeCount;
+    _writeCount += 1;
+    final error = writeError;
+    if (error != null || index == failWriteAtIndex) {
+      throw error ?? StateError('write $index failed');
+    }
     final bytes = <int>[];
     await for (final chunk in data) {
       bytes.addAll(chunk);
@@ -497,17 +538,21 @@ class FakeSftpSession implements SftpSession {
   @override
   Future<void> makeDirectory(String path) async {
     madeDirectories.add(path);
-    tree[path] = <SftpEntry>[];
+    tree.putIfAbsent(path, () => <SftpEntry>[]);
   }
 
   @override
   Future<void> rename(String from, String to) async {}
 
   @override
-  Future<void> delete(SftpEntry entry) async {}
+  Future<void> delete(SftpEntry entry) async {
+    deletedPaths.add(entry.path);
+  }
 
   @override
-  Future<void> close() async {}
+  Future<void> close() async {
+    closeCount += 1;
+  }
 }
 
 class RecordingFileExport implements FileExport {