diff --git a/apps/web/src/components/ChatView.tsx b/apps/web/src/components/ChatView.tsx
index 7994b3196f58edc031d943ab01ba4bc76347fd06..9e11132269e6bdae9284315e40776b04da5b5ea3 100644
--- a/apps/web/src/components/ChatView.tsx
+++ b/apps/web/src/components/ChatView.tsx
@@ -308,6 +308,8 @@ import {
 } from "../lib/composerContextRecords";
 import { type ReviewCommentContext } from "../reviewCommentContext";
 import { environmentCatalog } from "../connection/catalog";
+import { isDesktopLocalConnectionTarget } from "../connection/desktopLocal";
+import { useEnvironmentDisconnectDelay } from "../hooks/useEnvironmentDisconnectDelay";
 import { selectThreadTerminalUiState, useTerminalUiStateStore } from "../terminalUiStateStore";
 import { useKnownTerminalSessions, useThreadRunningTerminalIds } from "../state/terminalSessions";
 import { useEnvironmentQuery } from "../state/query";
@@ -1497,6 +1499,9 @@ export default function ChatView(props: ChatViewProps) {
   const { environments } = useEnvironments();
   const primaryEnvironment = usePrimaryEnvironment();
   const retryEnvironment = useAtomCommand(environmentCatalog.retryNow, { reportFailure: false });
+  const setEnvironmentEnabled = useAtomCommand(environmentCatalog.setEnabled, {
+    reportFailure: false,
+  });
   const environmentById = useMemo(
     () => new Map(environments.map((environment) => [environment.environmentId, environment])),
     [environments],
@@ -2208,6 +2213,37 @@ export default function ChatView(props: ChatViewProps) {
     },
     [retryEnvironment],
   );
+  const disconnectDelayElapsed = useEnvironmentDisconnectDelay(
+    activeEnvironmentUnavailable ? activeEnvironment.environmentId : null,
+  );
+  const canDisconnectActiveEnvironment =
+    disconnectDelayElapsed &&
+    activeEnvironment !== null &&
+    activeEnvironment.entry.target._tag !== "PrimaryConnectionTarget" &&
+    !isDesktopLocalConnectionTarget(activeEnvironment.entry.target);
+  const [disconnectingEnvironment, setDisconnectingEnvironment] = useState(false);
+  const handleDisconnectActiveEnvironment = useCallback(
+    async (environmentId: EnvironmentId) => {
+      setDisconnectingEnvironment(true);
+      const result = await setEnvironmentEnabled({ environmentId, enabled: false });
+      setDisconnectingEnvironment(false);
+      if (result._tag === "Failure") {
+        if (!isAtomCommandInterrupted(result)) {
+          const error = squashAtomCommandFailure(result);
+          toastManager.add(
+            stackedThreadToast({
+              type: "error",
+              title: "Could not disconnect server",
+              description: error instanceof Error ? error.message : "Failed to disconnect.",
+            }),
+          );
+        }
+        return;
+      }
+      void navigate({ to: "/", replace: true });
+    },
+    [navigate, setEnvironmentEnabled],
+  );
   const logicalProjectEnvironments = useMemo(() => {
     if (!activeProject) return [];
     const logicalKey = deriveLogicalProjectKeyFromSettings(activeProject, projectGroupingSettings);
@@ -2448,6 +2484,20 @@ export default function ChatView(props: ChatViewProps) {
     const items: ComposerBannerStackItem[] = [];
     const updateRunning = serverUpdateState.status === "running";
     const unavailableConnection = activeEnvironmentUnavailableState?.connection ?? null;
+    const disconnectAction =
+      canDisconnectActiveEnvironment && activeEnvironmentUnavailableState ? (
+        <Button
+          size="xs"
+          variant="ghost"
+          disabled={disconnectingEnvironment}
+          title="Hide this server's threads. Switch it on again in Connections."
+          onClick={() =>
+            void handleDisconnectActiveEnvironment(activeEnvironmentUnavailableState.environmentId)
+          }
+        >
+          Disconnect server
+        </Button>
+      ) : undefined;
     const environmentReconnecting =
       unavailableConnection !== null &&
       (unavailableConnection.phase === "connecting" ||
@@ -2481,6 +2531,7 @@ export default function ChatView(props: ChatViewProps) {
           ),
           title: `${unavailableConnection.phase === "connecting" ? "Connecting" : "Reconnecting"} to ${activeEnvironmentUnavailableState.label}`,
           description: "Finishing an update",
+          actions: disconnectAction,
         });
       } else {
         items.push({
@@ -2488,28 +2539,22 @@ export default function ChatView(props: ChatViewProps) {
           variant: unavailableConnection.phase === "error" ? "error" : "warning",
           icon: <WifiOffIcon />,
           title: `${activeEnvironmentUnavailableState.label} is ${environmentReconnecting ? "reconnecting" : "offline"}`,
-          description: environmentReconnecting ? "Trying again" : "Reconnect to continue",
           actions: (
             <>
-              <Button
-                size="xs"
-                variant="ghost"
-                disabled={environmentReconnecting}
-                onClick={() =>
-                  void handleReconnectActiveEnvironment(
-                    activeEnvironmentUnavailableState.environmentId,
-                  )
-                }
-              >
-                {environmentReconnecting ? "Reconnecting..." : "Reconnect"}
-              </Button>
-              <Button
-                size="xs"
-                variant="ghost"
-                onClick={() => void navigate({ to: "/settings/connections" })}
-              >
-                Connections
-              </Button>
+              {!environmentReconnecting ? (
+                <Button
+                  size="xs"
+                  variant="ghost"
+                  onClick={() =>
+                    void handleReconnectActiveEnvironment(
+                      activeEnvironmentUnavailableState.environmentId,
+                    )
+                  }
+                >
+                  Reconnect
+                </Button>
+              ) : null}
+              {disconnectAction}
             </>
           ),
         });
@@ -2564,22 +2609,22 @@ export default function ChatView(props: ChatViewProps) {
           (versionMismatchSelfUpdate !== "desktop-managed" || !versionMismatchDesktopAppUpdate)
             ? serverUpdateGuidance(versionMismatchSelfUpdate)
             : undefined,
-        actions:
-          updateInProgress ||
-          !versionMismatch ||
+        actions: updateInProgress ? (
+          disconnectAction
+        ) : !versionMismatch ||
           (versionMismatchSelfUpdate === "desktop-managed" &&
             !versionMismatchDesktopAppUpdate) ? undefined : (
-            <ServerUpdateAction
-              environmentId={serverUpdateEnvironmentId}
-              serverLabel={versionMismatchServerLabel}
-              selfUpdate={versionMismatchSelfUpdate}
-              desktopAppUpdate={versionMismatchDesktopAppUpdate}
-              threadContinuation={versionMismatchThreadContinuation}
-              targetVersion={versionMismatch.clientVersion}
-              label={updateFailed ? "Retry" : "Update"}
-              variant="ghost"
-            />
-          ),
+          <ServerUpdateAction
+            environmentId={serverUpdateEnvironmentId}
+            serverLabel={versionMismatchServerLabel}
+            selfUpdate={versionMismatchSelfUpdate}
+            desktopAppUpdate={versionMismatchDesktopAppUpdate}
+            threadContinuation={versionMismatchThreadContinuation}
+            targetVersion={versionMismatch.clientVersion}
+            label={updateFailed ? "Retry" : "Update"}
+            variant="ghost"
+          />
+        ),
         ...(updateInProgress || (!updateFailed && !versionMismatchDismissKey)
           ? {}
           : {
@@ -2603,7 +2648,9 @@ export default function ChatView(props: ChatViewProps) {
     activeEnvironmentUnavailableState,
     reconnectWarningGraceElapsed,
     handleReconnectActiveEnvironment,
-    navigate,
+    canDisconnectActiveEnvironment,
+    disconnectingEnvironment,
+    handleDisconnectActiveEnvironment,
     setDismissedVersionMismatchKey,
     showVersionMismatchBanner,
     serverUpdateFailureDismissed,
diff --git a/apps/web/src/hooks/useEnvironmentDisconnectDelay.test.tsx b/apps/web/src/hooks/useEnvironmentDisconnectDelay.test.tsx
new file mode 100644
index 0000000000000000000000000000000000000000..f584112df4dbdae0218940114721c81903e6edce
--- /dev/null
+++ b/apps/web/src/hooks/useEnvironmentDisconnectDelay.test.tsx
@@ -0,0 +1,65 @@
+import { EnvironmentId } from "@t3tools/contracts";
+import { act, useLayoutEffect } from "react";
+import { create, type ReactTestRenderer } from "react-test-renderer";
+import { afterEach, beforeEach, expect, it, vi } from "vite-plus/test";
+
+import { useEnvironmentDisconnectDelay } from "./useEnvironmentDisconnectDelay";
+
+const environmentId = EnvironmentId.make("remote");
+let renderer: ReactTestRenderer;
+let elapsed = false;
+
+function Probe({ unavailableId }: { unavailableId: EnvironmentId | null }) {
+  const value = useEnvironmentDisconnectDelay(unavailableId);
+  useLayoutEffect(() => {
+    elapsed = value;
+  });
+  return null;
+}
+
+beforeEach(() => {
+  vi.useFakeTimers();
+  vi.stubGlobal("IS_REACT_ACT_ENVIRONMENT", true);
+  act(() => {
+    renderer = create(<Probe unavailableId={environmentId} />);
+  });
+});
+
+afterEach(() => {
+  act(() => renderer.unmount());
+  vi.useRealTimers();
+  vi.unstubAllGlobals();
+});
+
+it("waits 20 seconds without restarting on renders for the same environment", () => {
+  act(() => vi.advanceTimersByTime(10_000));
+  expect(elapsed).toBe(false);
+  act(() => renderer.update(<Probe unavailableId={environmentId} />));
+  act(() => vi.advanceTimersByTime(9_999));
+  expect(elapsed).toBe(false);
+  act(() => vi.advanceTimersByTime(1));
+  expect(elapsed).toBe(true);
+});
+
+it("cancels a brief outage and starts a fresh delay on the next outage", () => {
+  act(() => vi.advanceTimersByTime(10_000));
+  act(() => renderer.update(<Probe unavailableId={null} />));
+  act(() => vi.advanceTimersByTime(20_000));
+  expect(elapsed).toBe(false);
+  act(() => renderer.update(<Probe unavailableId={environmentId} />));
+  act(() => vi.advanceTimersByTime(19_999));
+  expect(elapsed).toBe(false);
+  act(() => vi.advanceTimersByTime(1));
+  expect(elapsed).toBe(true);
+  act(() => renderer.update(<Probe unavailableId={null} />));
+  expect(elapsed).toBe(false);
+});
+
+it("does not carry elapsed time to another environment", () => {
+  act(() => vi.advanceTimersByTime(20_000));
+  expect(elapsed).toBe(true);
+  act(() => renderer.update(<Probe unavailableId={EnvironmentId.make("another-remote")} />));
+  expect(elapsed).toBe(false);
+  act(() => vi.advanceTimersByTime(20_000));
+  expect(elapsed).toBe(true);
+});
diff --git a/apps/web/src/hooks/useEnvironmentDisconnectDelay.ts b/apps/web/src/hooks/useEnvironmentDisconnectDelay.ts
new file mode 100644
index 0000000000000000000000000000000000000000..17c6f8f87be86923c9a22b1b7230d1e9561a52f3
--- /dev/null
+++ b/apps/web/src/hooks/useEnvironmentDisconnectDelay.ts
@@ -0,0 +1,25 @@
+import type { EnvironmentId } from "@t3tools/contracts";
+import { useEffect, useState } from "react";
+
+/** Wait through brief outages before offering to switch off the active environment. */
+export function useEnvironmentDisconnectDelay(unavailableEnvironmentId: EnvironmentId | null) {
+  const [delay, setDelay] = useState({ environmentId: unavailableEnvironmentId, elapsed: false });
+  if (delay.environmentId !== unavailableEnvironmentId) {
+    setDelay({ environmentId: unavailableEnvironmentId, elapsed: false });
+  }
+
+  useEffect(() => {
+    if (unavailableEnvironmentId === null) return;
+    const timeout = setTimeout(
+      () => setDelay({ environmentId: unavailableEnvironmentId, elapsed: true }),
+      20_000,
+    );
+    return () => clearTimeout(timeout);
+  }, [unavailableEnvironmentId]);
+
+  return (
+    unavailableEnvironmentId !== null &&
+    delay.environmentId === unavailableEnvironmentId &&
+    delay.elapsed
+  );
+}