diff --git a/apps/server/src/http.ts b/apps/server/src/http.ts
index 82de56b29b7..f759400f91e 100644
--- a/apps/server/src/http.ts
+++ b/apps/server/src/http.ts
@@ -43,6 +43,7 @@ import { browserApiCorsAllowedHeaders, browserApiCorsAllowedMethods } from "./ht
 import {
   contentCacheKey,
   isCompressibleContentType,
+  isContentHashedAsset,
   makeStaticCompressionCache,
   negotiateStaticEncoding,
   resolveStaticCacheControl,
@@ -389,19 +390,25 @@ export const staticAndDevRouteLayer = HttpRouter.add(
       data,
       contentType,
       cacheControl: resolveStaticCacheControl(staticRelativePath),
-      cacheKey: staticCacheKey(filePath, fileInfo),
+      // Hashed assets carry their content in their name, so metadata keying is
+      // both cheap and correct. Stable-name files (favicon, manifest, ...) can
+      // change content across a hot swap while keeping mtime/size, which would
+      // let the compression cache serve stale bytes -- key those by content,
+      // as index.html already is above.
+      cacheKey: isContentHashedAsset(staticRelativePath)
+        ? staticCacheKey(filePath, fileInfo)
+        : contentCacheKey(data),
       acceptEncoding: request.headers["accept-encoding"],
     });
   }),
 );
 
 /**
- * Identifies a build of a file for the compression cache, without hashing
- * payloads that can run to megabytes. The stat is taken before the bytes are
- * read, so a rebuild landing between the two can only orphan an entry under
- * the superseded key, never publish those bytes under the newer one. Files
- * whose contents change without their name are keyed by content instead; the
- * rest carry a content hash in their filename already.
+ * Identifies a build of a hashed asset for the compression cache without
+ * hashing payloads that can run to megabytes. Only used for files whose name
+ * already carries a content hash (see isContentHashedAsset), so the name
+ * changes whenever the bytes do and metadata keying cannot collide across a
+ * rebuild or hot swap. Stable-name files are keyed by content at the call site.
  */
 function staticCacheKey(filePath: string, info: FileSystem.File.Info): string {
   const mtimeMs = info.mtime.pipe(
diff --git a/apps/server/src/staticAssetDelivery.test.ts b/apps/server/src/staticAssetDelivery.test.ts
index 9f3eff34e33..c9e78f2c36d 100644
--- a/apps/server/src/staticAssetDelivery.test.ts
+++ b/apps/server/src/staticAssetDelivery.test.ts
@@ -3,6 +3,7 @@ import { describe, expect, it } from "vite-plus/test";
 import {
   contentCacheKey,
   isCompressibleContentType,
+  isContentHashedAsset,
   makeStaticCompressionCache,
   negotiateStaticEncoding,
   resolveStaticCacheControl,
@@ -26,6 +27,23 @@ describe("contentCacheKey", () => {
   });
 });
 
+describe("isContentHashedAsset", () => {
+  it("recognizes vite content-hashed bundle assets", () => {
+    expect(isContentHashedAsset("assets/index-DxV9k2Qp.js")).toBe(true);
+    expect(isContentHashedAsset("/assets/style-a1b2c3d4.css")).toBe(true);
+  });
+
+  it("rejects stable-name files that a hot swap can change in place", () => {
+    // These keep their name across builds, so the compression cache must key
+    // them by content, not path/mtime/size -- otherwise an atomic asset swap
+    // that preserves metadata could serve stale bytes.
+    expect(isContentHashedAsset("index.html")).toBe(false);
+    expect(isContentHashedAsset("favicon.ico")).toBe(false);
+    expect(isContentHashedAsset("manifest.webmanifest")).toBe(false);
+    expect(isContentHashedAsset("assets/logo.svg")).toBe(false);
+  });
+});
+
 describe("resolveStaticCacheControl", () => {
   it("marks content-hashed bundle assets immutable", () => {
     expect(resolveStaticCacheControl("assets/index-DxV9k2Qp.js")).toBe(
diff --git a/apps/server/src/staticAssetDelivery.ts b/apps/server/src/staticAssetDelivery.ts
index fa7d41ec255..5eb1136e3f8 100644
--- a/apps/server/src/staticAssetDelivery.ts
+++ b/apps/server/src/staticAssetDelivery.ts
@@ -38,11 +38,21 @@ const brotliCompress = NodeUtil.promisify(NodeZlib.brotliCompress);
 
 export type StaticContentEncoding = "br" | "gzip";
 
-export function resolveStaticCacheControl(relativePath: string): string {
+/**
+ * Whether a static file's name already encodes its content (a Vite hashed
+ * asset under `assets/`). Such files are safe to cache forever and safe to key
+ * by path/metadata, because the name changes whenever the bytes do. Every other
+ * served file keeps a stable name across builds, so a hot asset swap that
+ * preserves mtime and size could otherwise let the compression cache serve
+ * stale bytes -- those must be keyed by content instead.
+ */
+export function isContentHashedAsset(relativePath: string): boolean {
   const normalized = relativePath.replaceAll("\\", "/").replace(/^\/+/, "");
-  return normalized.startsWith("assets/") && HASHED_ASSET_PATTERN.test(normalized)
-    ? IMMUTABLE_CACHE_CONTROL
-    : REVALIDATE_CACHE_CONTROL;
+  return normalized.startsWith("assets/") && HASHED_ASSET_PATTERN.test(normalized);
+}
+
+export function resolveStaticCacheControl(relativePath: string): string {
+  return isContentHashedAsset(relativePath) ? IMMUTABLE_CACHE_CONTROL : REVALIDATE_CACHE_CONTROL;
 }
 
 /**
diff --git a/scripts/classify-deployment-diff.sh b/scripts/classify-deployment-diff.sh
index 66c6bea9c6a..7c5f13adc6b 100755
--- a/scripts/classify-deployment-diff.sh
+++ b/scripts/classify-deployment-diff.sh
@@ -41,6 +41,12 @@ printf 'Changed paths: %d runtime, %d non-runtime\n' \
   "${#runtime_paths[@]}" "${#non_runtime_paths[@]}"
 
 server=false
+# server_code tracks whether the SERVER PROCESS's own code (not just the web
+# bundle it serves) changed. apps/web changes leave server=true but keep the
+# server hot-swappable: the running process serves dist/client live from disk,
+# so new assets can be swapped in without a restart. Only a true server_code
+# change forces a process restart.
+server_code=false
 discord=false
 vscode=false
 mobile=false
@@ -48,6 +54,7 @@ desktop=false
 
 select_all() {
   server=true
+  server_code=true
   discord=true
   vscode=true
   mobile=true
@@ -70,10 +77,13 @@ for path in "${runtime_paths[@]}"; do
       ;;
     apps/server/*)
       server=true
+      server_code=true
       ;;
     apps/web/*)
       # The web application is served by both standalone servers and packaged
-      # desktop clients.
+      # desktop clients. It changes the served bundle but not the server process
+      # code, so the server can be hot-swapped (assets replaced on disk) rather
+      # than restarted. Desktop bundles its own copy, so it still rebuilds.
       server=true
       desktop=true
       ;;
@@ -95,6 +105,14 @@ if [[ "${server}" == "true" || "${discord}" == "true" || "${vscode}" == "true" |
   deploy=true
 fi
 
+# The server target is affected purely through its served web bundle (no server
+# process code changed), so ops can hot-swap dist/client on the running server
+# instead of restarting it. Desktop, if flagged, still rebuilds independently.
+web_hot_swap=false
+if [[ "${server}" == "true" && "${server_code}" == "false" ]]; then
+  web_hot_swap=true
+fi
+
 if [[ "${deploy}" == "true" ]]; then
   printf 'Runtime-affecting paths:\n'
   printf '  %s\n' "${runtime_paths[@]}"
@@ -104,6 +122,7 @@ fi
 
 printf 'deploy=%s\n' "${deploy}"
 printf 'server=%s\n' "${server}"
+printf 'web_hot_swap=%s\n' "${web_hot_swap}"
 printf 'discord=%s\n' "${discord}"
 printf 'vscode=%s\n' "${vscode}"
 printf 'mobile=%s\n' "${mobile}"
diff --git a/scripts/classify-deployment-diff.test.sh b/scripts/classify-deployment-diff.test.sh
index d0c2a00621d..b11346eadb8 100755
--- a/scripts/classify-deployment-diff.test.sh
+++ b/scripts/classify-deployment-diff.test.sh
@@ -41,10 +41,16 @@ assert_scope apps/discord-bot/src/main.ts $'deploy=true\ndiscord=true\nserver=fa
 assert_scope apps/vscode/src/extension.ts $'deploy=true\ndiscord=false\nserver=false\nvscode=true\nmobile=false\ndesktop=false'
 assert_scope apps/mobile/src/App.tsx $'deploy=true\ndiscord=false\nserver=false\nvscode=false\nmobile=true\ndesktop=false'
 assert_scope apps/desktop/src/main.ts $'deploy=true\ndiscord=false\nserver=false\nvscode=false\nmobile=false\ndesktop=true'
-assert_scope apps/server/src/server.ts $'deploy=true\ndiscord=false\nserver=true\nvscode=false\nmobile=false\ndesktop=false'
-assert_scope apps/web/src/App.tsx $'deploy=true\ndiscord=false\nserver=true\nvscode=false\nmobile=false\ndesktop=true'
-assert_scope packages/client-runtime/src/index.ts $'deploy=true\ndiscord=true\nserver=true\nvscode=true\nmobile=true\ndesktop=true'
-assert_scope pnpm-lock.yaml $'deploy=true\ndiscord=true\nserver=true\nvscode=true\nmobile=true\ndesktop=true'
-assert_scope docs/deployment.md $'deploy=false\ndiscord=false\nserver=false\nvscode=false\nmobile=false\ndesktop=false'
+# Server process code changed -> must restart, not hot-swap.
+assert_scope apps/server/src/server.ts $'deploy=true\ndiscord=false\nserver=true\nvscode=false\nmobile=false\ndesktop=false\nweb_hot_swap=false'
+# Web-only change -> server target affected purely via its served bundle, so it
+# is hot-swappable (assets replaced on the running server); desktop still rebuilds.
+assert_scope apps/web/src/App.tsx $'deploy=true\ndiscord=false\nserver=true\nvscode=false\nmobile=false\ndesktop=true\nweb_hot_swap=true'
+# Cross-boundary packages force a full restart, so no hot-swap.
+assert_scope packages/client-runtime/src/index.ts $'deploy=true\ndiscord=true\nserver=true\nvscode=true\nmobile=true\ndesktop=true\nweb_hot_swap=false'
+assert_scope pnpm-lock.yaml $'deploy=true\ndiscord=true\nserver=true\nvscode=true\nmobile=true\ndesktop=true\nweb_hot_swap=false'
+# Discord-only change never touches the server, so no web hot-swap either.
+assert_scope apps/discord-bot/src/handler.ts $'deploy=true\nserver=false\nweb_hot_swap=false'
+assert_scope docs/deployment.md $'deploy=false\ndiscord=false\nserver=false\nvscode=false\nmobile=false\ndesktop=false\nweb_hot_swap=false'
 
 echo "deployment classifier tests passed"