diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3dc19cf5..4fe2e355 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -32,6 +32,7 @@ For more information about each release including git tags and artifacts, see [R
 - Event stream shows sensible defaults so first-load isn't empty ([#297](https://github.com/roostorg/osprey/pull/297) by [@haileyok](https://github.com/haileyok))
 - Replace `react-scripts` with `rsbuild`/`rspack` for UI builds ([#235](https://github.com/roostorg/osprey/pull/235) by [@chimosky](https://github.com/chimosky))
 - Migrate from npm to pnpm via Corepack ([#252](https://github.com/roostorg/osprey/pull/252) by [@haileyok](https://github.com/haileyok))
+- Upgrade `grpcio` from 1.49.1/1.53.x to 1.82.1, and `typing-extensions` from 4.6.3 to 4.12.2 (required by the grpcio upgrade) ([#415](https://github.com/roostorg/osprey/pull/415) by [@reitblatt](https://github.com/reitblatt))
 
 ### Fixed
 
diff --git a/pyproject.toml b/pyproject.toml
index cf10a8b9..1850570b 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -26,8 +26,7 @@ common = [
     "graphviz==0.20",
     "greenlet",
     "grpc-google-iam-v1==0.14.2",
-    "grpcio==1.49.1; platform_machine == 'x86_64'",
-    "grpcio==1.53.*; platform_machine != 'x86_64'",
+    "grpcio==1.82.1",
     "grpcio-health-checking==1.44.0",
     "grpcio-reflection==1.44.0",
     "grpcio-status==1.49.1; platform_machine == 'x86_64'",
diff --git a/uv.lock b/uv.lock
index 94209888..3c967f86 100644
--- a/uv.lock
+++ b/uv.lock
@@ -47,8 +47,7 @@ common = [
     { name = "graphviz", specifier = "==0.20" },
     { name = "greenlet", git = "https://github.com/discord/greenlet.git?rev=a75d78f1547c74a81134644a179467525a255466" },
     { name = "grpc-google-iam-v1", specifier = "==0.14.2" },
-    { name = "grpcio", marker = "platform_machine != 'x86_64'", specifier = "==1.53.*" },
-    { name = "grpcio", marker = "platform_machine == 'x86_64'", specifier = "==1.49.1" },
+    { name = "grpcio", specifier = "==1.82.1" },
     { name = "grpcio-health-checking", specifier = "==1.44.0" },
     { name = "grpcio-reflection", specifier = "==1.44.0" },
     { name = "grpcio-status", marker = "platform_machine != 'x86_64'", specifier = "==1.53.*" },
@@ -648,8 +647,7 @@ wheels = [
 
 [package.optional-dependencies]
 grpc = [
-    { name = "grpcio", version = "1.49.1", source = { registry = "https://pypi.org/simple" }, marker = "platform_machine == 'x86_64'" },
-    { name = "grpcio", version = "1.53.2", source = { registry = "https://pypi.org/simple" }, marker = "platform_machine != 'x86_64'" },
+    { name = "grpcio" },
     { name = "grpcio-status", version = "1.49.1", source = { registry = "https://pypi.org/simple" }, marker = "platform_machine == 'x86_64'" },
     { name = "grpcio-status", version = "1.53.2", source = { registry = "https://pypi.org/simple" }, marker = "platform_machine != 'x86_64'" },
 ]
@@ -737,8 +735,7 @@ source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "google-api-core", extra = ["grpc"] },
     { name = "grpc-google-iam-v1" },
-    { name = "grpcio", version = "1.49.1", source = { registry = "https://pypi.org/simple" }, marker = "platform_machine == 'x86_64'" },
-    { name = "grpcio", version = "1.53.2", source = { registry = "https://pypi.org/simple" }, marker = "platform_machine != 'x86_64'" },
+    { name = "grpcio" },
     { name = "grpcio-status", version = "1.49.1", source = { registry = "https://pypi.org/simple" }, marker = "platform_machine == 'x86_64'" },
     { name = "grpcio-status", version = "1.53.2", source = { registry = "https://pypi.org/simple" }, marker = "platform_machine != 'x86_64'" },
     { name = "proto-plus" },
@@ -821,8 +818,7 @@ wheels = [
 
 [package.optional-dependencies]
 grpc = [
-    { name = "grpcio", version = "1.49.1", source = { registry = "https://pypi.org/simple" }, marker = "platform_machine == 'x86_64'" },
-    { name = "grpcio", version = "1.53.2", source = { registry = "https://pypi.org/simple" }, marker = "platform_machine != 'x86_64'" },
+    { name = "grpcio" },
 ]
 
 [[package]]
@@ -845,8 +841,7 @@ version = "0.14.2"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "googleapis-common-protos", extra = ["grpc"] },
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-    { name = "grpcio", version = "1.53.2", source = { registry = "https://pypi.org/simple" }, marker = "platform_machine != 'x86_64'" },
+    { name = "grpcio" },
     { name = "protobuf" },
 ]
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@@ -856,49 +851,53 @@ wheels = [
 
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