diff --git a/apps/emdash-desktop/src/main/core/agent-hooks/claude-trust-service.test.ts b/apps/emdash-desktop/src/main/core/agent-hooks/claude-trust-service.test.ts
index 2cfc4427be..e57854def5 100644
--- a/apps/emdash-desktop/src/main/core/agent-hooks/claude-trust-service.test.ts
+++ b/apps/emdash-desktop/src/main/core/agent-hooks/claude-trust-service.test.ts
@@ -281,6 +281,7 @@ describe('ClaudeTrustService', () => {
     const ctx: IExecutionContext = {
       root: undefined,
       supportsLocalSpawn: false,
+      isWindows: false,
       exec: vi.fn().mockImplementation(async (command: string, args: string[] = []) => {
         if (command === 'sh') {
           return { stdout: '/home/remote-user', stderr: '' };
diff --git a/apps/emdash-desktop/src/main/core/agent-hooks/cursor-trust-service.test.ts b/apps/emdash-desktop/src/main/core/agent-hooks/cursor-trust-service.test.ts
index 08f4f3f03d..35174a4842 100644
--- a/apps/emdash-desktop/src/main/core/agent-hooks/cursor-trust-service.test.ts
+++ b/apps/emdash-desktop/src/main/core/agent-hooks/cursor-trust-service.test.ts
@@ -67,6 +67,7 @@ function makeCtx(): IExecutionContext {
   return {
     root: undefined,
     supportsLocalSpawn: false,
+    isWindows: false,
     exec: vi.fn().mockImplementation(async (command: string) => {
       if (command === 'sh') return { stdout: '/home/remote-user', stderr: '' };
       return { stdout: '', stderr: '' };
diff --git a/apps/emdash-desktop/src/main/core/agent-hooks/hook-config.test.ts b/apps/emdash-desktop/src/main/core/agent-hooks/hook-config.test.ts
index 43c64a0e20..eed3a60947 100644
--- a/apps/emdash-desktop/src/main/core/agent-hooks/hook-config.test.ts
+++ b/apps/emdash-desktop/src/main/core/agent-hooks/hook-config.test.ts
@@ -13,6 +13,7 @@ vi.mock('@main/core/dependencies/probe', () => ({
 function makeExecutionContext(): IExecutionContext {
   return {
     supportsLocalSpawn: false,
+    isWindows: false,
     exec: vi.fn(async () => ({ stdout: '', stderr: '' })),
     execStreaming: vi.fn(async () => {}),
     dispose: vi.fn(),
diff --git a/apps/emdash-desktop/src/main/core/agent-hooks/workspace-trust-service.test.ts b/apps/emdash-desktop/src/main/core/agent-hooks/workspace-trust-service.test.ts
index d325c48138..0eccdd2e38 100644
--- a/apps/emdash-desktop/src/main/core/agent-hooks/workspace-trust-service.test.ts
+++ b/apps/emdash-desktop/src/main/core/agent-hooks/workspace-trust-service.test.ts
@@ -19,6 +19,7 @@ function makeCtx(): IExecutionContext {
   return {
     root: undefined,
     supportsLocalSpawn: false,
+    isWindows: false,
     exec: vi.fn(),
     execStreaming: vi.fn(),
     dispose: vi.fn(),
diff --git a/apps/emdash-desktop/src/main/core/dependencies/probe.test.ts b/apps/emdash-desktop/src/main/core/dependencies/probe.test.ts
new file mode 100644
index 0000000000..e8c355646b
--- /dev/null
+++ b/apps/emdash-desktop/src/main/core/dependencies/probe.test.ts
@@ -0,0 +1,72 @@
+import { describe, expect, it, vi } from 'vitest';
+import type { IExecutionContext } from '@main/core/execution-context/types';
+import { resolveCommandPath } from './probe';
+
+function makeCtx(
+  isWindows: boolean,
+  handler: (command: string, args: string[]) => Promise<{ stdout: string; stderr: string }>
+): IExecutionContext {
+  return {
+    root: undefined,
+    supportsLocalSpawn: false,
+    isWindows,
+    exec: vi.fn().mockImplementation(handler),
+    execStreaming: vi.fn(),
+    dispose: vi.fn(),
+  } as unknown as IExecutionContext;
+}
+
+describe('resolveCommandPath', () => {
+  it('uses `which` on POSIX hosts', async () => {
+    const ctx = makeCtx(false, async () => ({ stdout: '/usr/local/bin/claude\n', stderr: '' }));
+
+    const path = await resolveCommandPath('claude', ctx);
+
+    expect(ctx.exec).toHaveBeenCalledWith('which', ['claude'], { timeout: 5000 });
+    expect(path).toBe('/usr/local/bin/claude');
+  });
+
+  it('uses `where` on Windows hosts', async () => {
+    const ctx = makeCtx(true, async () => ({ stdout: 'C:\\bin\\claude.exe\n', stderr: '' }));
+
+    const path = await resolveCommandPath('claude', ctx);
+
+    expect(ctx.exec).toHaveBeenCalledWith('where', ['claude'], { timeout: 5000 });
+    expect(path).toBe('C:\\bin\\claude.exe');
+  });
+
+  // Regression: a Windows client connected to a POSIX remote over SSH must run
+  // `which` on the remote host, not `where`. The resolve command follows the
+  // execution context's platform, never the local client's. See issue #2474.
+  it('uses `which` for a POSIX SSH context even when the client is Windows', async () => {
+    const ctx = makeCtx(false, async () => ({
+      stdout: '/home/dev/.local/bin/claude\n',
+      stderr: '',
+    }));
+
+    const path = await resolveCommandPath('claude', ctx);
+
+    expect(ctx.exec).toHaveBeenCalledWith('which', ['claude'], { timeout: 5000 });
+    expect(ctx.exec).not.toHaveBeenCalledWith('where', expect.anything(), expect.anything());
+    expect(path).toBe('/home/dev/.local/bin/claude');
+  });
+
+  it('returns the first match and trims surrounding whitespace', async () => {
+    const ctx = makeCtx(true, async () => ({
+      stdout: 'C:\\bin\\claude.exe\r\nC:\\other\\claude.exe\r\n',
+      stderr: '',
+    }));
+
+    const path = await resolveCommandPath('claude', ctx);
+
+    expect(path).toBe('C:\\bin\\claude.exe');
+  });
+
+  it('returns null when resolution fails', async () => {
+    const ctx = makeCtx(false, async () => {
+      throw new Error('not found');
+    });
+
+    expect(await resolveCommandPath('claude', ctx)).toBeNull();
+  });
+});
diff --git a/apps/emdash-desktop/src/main/core/dependencies/probe.ts b/apps/emdash-desktop/src/main/core/dependencies/probe.ts
index 6baeeb760e..4b676c57cf 100644
--- a/apps/emdash-desktop/src/main/core/dependencies/probe.ts
+++ b/apps/emdash-desktop/src/main/core/dependencies/probe.ts
@@ -4,12 +4,16 @@ import type { ProbeResult } from './types';
 const WHICH_TIMEOUT_MS = 5_000;
 const VERSION_PROBE_TIMEOUT_MS = 10_000;
 
-// `where` on Windows, `which` on macOS/Linux
-const RESOLVE_CMD = process.platform === 'win32' ? 'where' : 'which';
+// The resolve command must match the platform the context executes on, not the
+// local client: a Windows client connected to a POSIX remote over SSH must run
+// `which` on the remote host, never `where`.
+function resolveCmd(ctx: IExecutionContext): string {
+  return ctx.isWindows ? 'where' : 'which';
+}
 
 /**
  * Resolves the absolute path of a command binary.
- * Uses `where` on Windows and `which` on macOS/Linux.
+ * Uses `where` on Windows hosts and `which` on macOS/Linux hosts.
  * Returns `null` if the command is not found or the resolution fails.
  */
 export async function resolveCommandPath(
@@ -17,7 +21,7 @@ export async function resolveCommandPath(
   ctx: IExecutionContext
 ): Promise<string | null> {
   try {
-    const { stdout } = await ctx.exec(RESOLVE_CMD, [command], { timeout: WHICH_TIMEOUT_MS });
+    const { stdout } = await ctx.exec(resolveCmd(ctx), [command], { timeout: WHICH_TIMEOUT_MS });
     const firstLine = stdout.trim().split('\n')[0]?.trim();
     return firstLine ?? null;
   } catch {
diff --git a/apps/emdash-desktop/src/main/core/execution-context/local-execution-context.ts b/apps/emdash-desktop/src/main/core/execution-context/local-execution-context.ts
index 11e2af2959..0f12d8bbb7 100644
--- a/apps/emdash-desktop/src/main/core/execution-context/local-execution-context.ts
+++ b/apps/emdash-desktop/src/main/core/execution-context/local-execution-context.ts
@@ -20,6 +20,7 @@ function buildNonInteractiveGitEnv(): NodeJS.ProcessEnv {
 export class LocalExecutionContext implements IExecutionContext {
   readonly root: string;
   readonly supportsLocalSpawn = true;
+  readonly isWindows = process.platform === 'win32';
 
   private readonly _lifetime = new AbortController();
 
diff --git a/apps/emdash-desktop/src/main/core/execution-context/ssh-execution-context.ts b/apps/emdash-desktop/src/main/core/execution-context/ssh-execution-context.ts
index 4405a6369b..7626c43f0a 100644
--- a/apps/emdash-desktop/src/main/core/execution-context/ssh-execution-context.ts
+++ b/apps/emdash-desktop/src/main/core/execution-context/ssh-execution-context.ts
@@ -37,6 +37,7 @@ export function buildSshCommand(
 export class SshExecutionContext implements IExecutionContext {
   readonly root?: string;
   readonly supportsLocalSpawn = false;
+  readonly isWindows = false;
 
   private readonly _lifetime = new AbortController();
 
diff --git a/apps/emdash-desktop/src/main/core/execution-context/types.ts b/apps/emdash-desktop/src/main/core/execution-context/types.ts
index 50ebc5da7d..012ecda778 100644
--- a/apps/emdash-desktop/src/main/core/execution-context/types.ts
+++ b/apps/emdash-desktop/src/main/core/execution-context/types.ts
@@ -24,6 +24,15 @@ export interface IExecutionContext {
    */
   readonly supportsLocalSpawn: boolean;
 
+  /**
+   * Whether the host this context executes on is Windows. Consumers must use
+   * this — not the local `process.platform` — when picking platform-specific
+   * commands (e.g. `where` vs `which`), so a Windows client connected to a
+   * POSIX remote over SSH still runs the right command on the remote host.
+   * SSH remotes are POSIX, so this is always false for them.
+   */
+  readonly isWindows: boolean;
+
   /** Run a command and buffer all output. Rejects on non-zero exit code. */
   exec(command: string, args?: string[], opts?: ExecOptions): Promise<ExecResult>;
 
diff --git a/apps/emdash-desktop/src/main/core/git/impl/git-service.test.ts b/apps/emdash-desktop/src/main/core/git/impl/git-service.test.ts
index ed19d08a26..1ee14a523d 100644
--- a/apps/emdash-desktop/src/main/core/git/impl/git-service.test.ts
+++ b/apps/emdash-desktop/src/main/core/git/impl/git-service.test.ts
@@ -49,6 +49,7 @@ function makeContext(exec: MockExec, root = '/repo'): IExecutionContext {
   return {
     root,
     supportsLocalSpawn: false,
+    isWindows: false,
     exec: (_cmd, args = [], _opts) => exec(_cmd, args),
     execStreaming: async (_cmd, _args, onChunk) => {
       onChunk('');
diff --git a/apps/emdash-desktop/src/main/core/projects/worktrees/worktree-service.test.ts b/apps/emdash-desktop/src/main/core/projects/worktrees/worktree-service.test.ts
index d238f8e8a9..3c8e4278af 100644
--- a/apps/emdash-desktop/src/main/core/projects/worktrees/worktree-service.test.ts
+++ b/apps/emdash-desktop/src/main/core/projects/worktrees/worktree-service.test.ts
@@ -99,6 +99,7 @@ describe('WorktreeService', () => {
     const remoteCtx = {
       root: '/remote/repo',
       supportsLocalSpawn: false,
+      isWindows: false,
       exec: vi.fn().mockResolvedValue({ stdout: '', stderr: '' }),
       execStreaming: vi.fn().mockResolvedValue(undefined),
       dispose: vi.fn(),
@@ -149,6 +150,7 @@ describe('WorktreeService', () => {
       const ctx: IExecutionContext = {
         root: repoDir,
         supportsLocalSpawn: false,
+        isWindows: false,
         exec,
         execStreaming: async () => {},
         dispose: () => {},
@@ -228,6 +230,7 @@ describe('WorktreeService', () => {
       const ctx: IExecutionContext = {
         root: repoDir,
         supportsLocalSpawn: false,
+        isWindows: false,
         exec,
         execStreaming: async () => {},
         dispose: () => {},
@@ -306,6 +309,7 @@ describe('WorktreeService', () => {
       const ctx: IExecutionContext = {
         root: repoDir,
         supportsLocalSpawn: false,
+        isWindows: false,
         exec,
         execStreaming: async () => {},
         dispose: () => {},
@@ -431,6 +435,7 @@ describe('WorktreeService', () => {
       const ctx: IExecutionContext = {
         root: repoDir,
         supportsLocalSpawn: false,
+        isWindows: false,
         exec,
         execStreaming: async () => {},
         dispose: () => {},
diff --git a/apps/emdash-desktop/src/main/core/terminals/impl/local-terminal-provider.test.ts b/apps/emdash-desktop/src/main/core/terminals/impl/local-terminal-provider.test.ts
index f21913237b..0b7fc528ad 100644
--- a/apps/emdash-desktop/src/main/core/terminals/impl/local-terminal-provider.test.ts
+++ b/apps/emdash-desktop/src/main/core/terminals/impl/local-terminal-provider.test.ts
@@ -43,6 +43,7 @@ const terminal: Terminal = {
 
 const ctx = {
   supportsLocalSpawn: true,
+  isWindows: false,
   exec: vi.fn(),
   execStreaming: vi.fn(),
   dispose: vi.fn(),
diff --git a/apps/emdash-desktop/src/main/core/terminals/impl/ssh-terminal-provider.test.ts b/apps/emdash-desktop/src/main/core/terminals/impl/ssh-terminal-provider.test.ts
index dd47be926e..d0cbfae4b9 100644
--- a/apps/emdash-desktop/src/main/core/terminals/impl/ssh-terminal-provider.test.ts
+++ b/apps/emdash-desktop/src/main/core/terminals/impl/ssh-terminal-provider.test.ts
@@ -54,6 +54,7 @@ const terminal: Terminal = {
 
 const ctx = {
   supportsLocalSpawn: false,
+  isWindows: false,
   exec: vi.fn(),
   execStreaming: vi.fn(),
   dispose: vi.fn(),
diff --git a/apps/emdash-desktop/src/main/db/legacy-port/importers/relational/relational.test.ts b/apps/emdash-desktop/src/main/db/legacy-port/importers/relational/relational.test.ts
index de0337877b..4b30c31f5e 100644
--- a/apps/emdash-desktop/src/main/db/legacy-port/importers/relational/relational.test.ts
+++ b/apps/emdash-desktop/src/main/db/legacy-port/importers/relational/relational.test.ts
@@ -677,6 +677,7 @@ describe('legacy-port table passes', () => {
     const tmuxExec = {
       root: undefined,
       supportsLocalSpawn: false,
+      isWindows: false,
       exec: async (command: string, args: string[] = []) => {
         calls.push({ command, args });
         if (