diff --git a/apps/web/src/components/ChatView.tsx b/apps/web/src/components/ChatView.tsx
index 9621f5f167484b6b272ec300e3cb3dae4883c02f..d8ca76677e3ccd5db2c2cf5eabada5e8cd11eab5 100644
--- a/apps/web/src/components/ChatView.tsx
+++ b/apps/web/src/components/ChatView.tsx
@@ -160,7 +160,6 @@ import {
   CheckCircle2Icon,
   ChevronDownIcon,
   GitBranchIcon,
-  TriangleAlertIcon,
   WifiOffIcon,
 } from "lucide-react";
 import { cn, randomHex } from "~/lib/utils";
@@ -1986,31 +1985,35 @@ function ChatViewContent(props: ChatViewProps) {
       const updateFailed = serverUpdateState.status === "failed";
       items.push({
         id: `server-version:${serverUpdateEnvironmentId}`,
-        variant: updateFailed ? "error" : updateInProgress ? "default" : "warning",
-        icon: updateInProgress ? (
-          <span
-            className="size-1.5 animate-status-pulse rounded-full bg-foreground"
-            aria-hidden="true"
-          />
-        ) : (
-          <TriangleAlertIcon />
-        ),
+        variant: updateFailed ? "error" : "default",
+        // In-flight and failed states carry their own status dot inside
+        // ServerUpdateProgress; only the idle offer needs an icon.
+        icon:
+          updateInProgress || updateFailed ? null : (
+            <span
+              className="size-1.5 rounded-full border border-muted-foreground/40"
+              aria-hidden="true"
+            />
+          ),
         title:
-          updateInProgress || updateFailed
-            ? `${updateFailed ? "Could not update" : "Updating"} ${versionMismatchServerLabel}`
-            : "Client and server versions differ",
-        description:
           updateInProgress || updateFailed ? (
-            <ServerUpdateProgress
-              fromVersion={serverUpdateState.fromVersion}
-              state={serverUpdateState}
-            />
+            `${updateFailed ? "Could not update" : "Updating"} ${versionMismatchServerLabel}`
           ) : versionMismatch ? (
-            <>
-              Client {versionMismatch.clientVersion} is connected to {versionMismatchServerLabel}{" "}
-              {versionMismatch.serverVersion}.{" "}
-              {serverUpdateGuidance(versionMismatchSelfUpdate, versionMismatchServerLabel)}
-            </>
+            <Tooltip>
+              <TooltipTrigger render={<span>Server update available</span>} />
+              <TooltipPopup side="top">
+                {versionMismatchServerLabel} {versionMismatch.serverVersion}{" "}
+                <span aria-hidden="true">→</span> {versionMismatch.clientVersion}
+              </TooltipPopup>
+            </Tooltip>
+          ) : (
+            "Server update available"
+          ),
+        description:
+          updateInProgress || updateFailed ? (
+            <ServerUpdateProgress state={serverUpdateState} />
+          ) : versionMismatchSelfUpdate === "desktop-managed" ? (
+            serverUpdateGuidance(versionMismatchSelfUpdate, versionMismatchServerLabel)
           ) : null,
         // The desktop-managed guidance is already the description; the action
         // slot would only repeat it.
@@ -2023,13 +2026,13 @@ function ChatViewContent(props: ChatViewProps) {
               serverLabel={versionMismatchServerLabel}
               selfUpdate={versionMismatchSelfUpdate}
               targetVersion={versionMismatch.clientVersion}
-              {...(updateFailed ? { label: "Retry update" } : {})}
+              label={updateFailed ? "Retry" : "Update"}
             />
           ),
         ...(updateInProgress || updateFailed || !versionMismatchDismissKey
           ? {}
           : {
-              dismissLabel: "Dismiss version mismatch warning",
+              dismissLabel: "Dismiss update notice",
               onDismiss: () => {
                 dismissVersionMismatch(versionMismatchDismissKey);
                 setDismissedVersionMismatchKey(versionMismatchDismissKey);
diff --git a/apps/web/src/components/ServerUpdateAction.test.tsx b/apps/web/src/components/ServerUpdateAction.test.tsx
index 4d5669a0a8ff950af8dfaf6445226364edc495e6..2928848959f245e7f029187ed56af23e46b75ad6 100644
--- a/apps/web/src/components/ServerUpdateAction.test.tsx
+++ b/apps/web/src/components/ServerUpdateAction.test.tsx
@@ -101,10 +101,9 @@ describe("ServerUpdateAction", () => {
 });
 
 describe("ServerUpdateProgress", () => {
-  it("renders the monochrome step rail with only the active step highlighted", () => {
+  it("shows one calm status row for the restart wait", () => {
     const markup = renderToStaticMarkup(
       <ServerUpdateProgress
-        fromVersion="0.0.30"
         state={{
           status: "running",
           stage: "resuming",
@@ -114,23 +113,36 @@ describe("ServerUpdateProgress", () => {
       />,
     );
 
-    expect(markup).toContain("0.0.30");
-    expect(markup).toContain("0.0.31");
-    expect(markup).toContain("Download");
-    expect(markup).toContain("Install");
-    expect(markup).toContain("Resuming");
-    // The wait state is monochrome and calm: no success/warning colors, no
-    // status sentence, one duty-cycled pulse on the active step.
+    expect(markup).toContain("Restarting…");
+    // The wait state is monochrome and calm: no versions, no step rail, no
+    // success/warning colors, one duty-cycled pulse on the dot.
+    expect(markup).not.toContain("0.0.30");
+    expect(markup).not.toContain("Resum");
     expect(markup).not.toContain("text-success");
     expect(markup).not.toContain("text-primary");
     expect(markup).toContain("animate-status-pulse");
     expect(markup).not.toContain("animate-spin");
   });
 
-  it("keeps the failed stage visible with its retryable error", () => {
+  it("folds the sub-second installing handoff into the download phase", () => {
+    const markup = renderToStaticMarkup(
+      <ServerUpdateProgress
+        state={{
+          status: "running",
+          stage: "installing",
+          fromVersion: "0.0.30",
+          targetVersion: "0.0.31",
+        }}
+      />,
+    );
+
+    expect(markup).toContain("Downloading…");
+    expect(markup).not.toContain("Install");
+  });
+
+  it("keeps the failure visible with its retryable error", () => {
     const markup = renderToStaticMarkup(
       <ServerUpdateProgress
-        fromVersion="0.0.30"
         state={{
           status: "failed",
           stage: "installing",
diff --git a/apps/web/src/components/ServerUpdateAction.tsx b/apps/web/src/components/ServerUpdateAction.tsx
index f3b6c694fae7dc71241fc52f2b770ad39e1c9f24..40d55e3a544c30bb438f6b05b318a98fe0704800 100644
--- a/apps/web/src/components/ServerUpdateAction.tsx
+++ b/apps/web/src/components/ServerUpdateAction.tsx
@@ -1,110 +1,63 @@
 import type { EnvironmentId, ServerSelfUpdateCapability } from "@t3tools/contracts";
-import type { ServerUpdateState } from "@t3tools/client-runtime/state/server";
+import type { ServerUpdateStage, ServerUpdateState } from "@t3tools/client-runtime/state/server";
 import {
   isAtomCommandInterrupted,
   squashAtomCommandFailure,
 } from "@t3tools/client-runtime/state/runtime";
-import { CheckIcon } from "lucide-react";
 
 import { useCopyToClipboard } from "~/hooks/useCopyToClipboard";
-import { cn } from "~/lib/utils";
 import { serverEnvironment } from "~/state/server";
 import { useAtomCommand } from "~/state/use-atom-command";
 import { manualServerUpdateCommand } from "~/versionSkew";
 import { Button } from "./ui/button";
 import { toastManager } from "./ui/toast";
 
-const UPDATE_STEPS = [
-  { stage: "downloading", label: "Download", activeLabel: "Downloading" },
-  { stage: "installing", label: "Install", activeLabel: "Installing" },
-  { stage: "resuming", label: "Resume", activeLabel: "Resuming" },
-] as const;
+// The wire "installing" stage is a sub-second launcher handoff, so the UI
+// folds it into the download phase; everything after the handoff is the
+// restart the user is actually waiting through.
+const UPDATE_STAGE_LABELS: Record<ServerUpdateStage, string> = {
+  downloading: "Downloading…",
+  installing: "Downloading…",
+  resuming: "Restarting…",
+};
 const pendingUpdateEnvironmentIds = new Set<EnvironmentId>();
 
+export function serverUpdateStageLabel(stage: ServerUpdateStage): string {
+  return UPDATE_STAGE_LABELS[stage];
+}
+
 function updateFailureMessage(error: unknown): string {
   return error instanceof Error ? error.message : "Server update failed.";
 }
 
 /**
- * Monochrome step rail for an in-flight server update. The update is a
- * wait, not a warning: done steps recede to gray, the active step is the
- * only bright element and pulses. Failure keeps the rail but surfaces the
- * error below it.
+ * One-row status for an in-flight server update: "Downloading…" then
+ * "Restarting…". The update is a wait, not a warning: a single pulsing dot
+ * and label, no step rail, no versions. Failure turns the row red with the
+ * rollback reason.
  */
 export function ServerUpdateProgress({
-  fromVersion,
   state,
 }: {
-  readonly fromVersion: string;
   readonly state: Exclude<ServerUpdateState, { status: "idle" }>;
 }) {
-  const currentIndex = UPDATE_STEPS.findIndex(({ stage }) => stage === state.stage);
-
-  return (
-    <div className="mt-1 min-w-0 space-y-2.5">
-      <p className="text-xs text-muted-foreground/70">
-        {fromVersion} <span aria-hidden="true">→</span> {state.targetVersion}
-      </p>
-      <ol className="flex min-w-0 items-center" aria-label="Server update progress">
-        {UPDATE_STEPS.map((step, index) => {
-          const complete = index < currentIndex;
-          const current = index === currentIndex;
-          const failed = current && state.status === "failed";
-          const running = current && state.status === "running";
-          return (
-            <li
-              key={step.stage}
-              className={cn(
-                "flex min-w-0 items-center text-xs font-medium",
-                index < UPDATE_STEPS.length - 1 ? "flex-1" : null,
-                complete
-                  ? "text-muted-foreground"
-                  : failed
-                    ? "text-destructive"
-                    : running
-                      ? "animate-status-pulse text-foreground"
-                      : "text-muted-foreground/50",
-              )}
-              aria-current={running ? "step" : undefined}
-            >
-              {complete ? (
-                <CheckIcon
-                  className="size-3.5 shrink-0 opacity-70"
-                  strokeWidth={2.5}
-                  aria-hidden="true"
-                />
-              ) : (
-                <span
-                  className={cn(
-                    "size-1.5 shrink-0 rounded-full",
-                    failed
-                      ? "bg-destructive"
-                      : running
-                        ? "bg-foreground"
-                        : "border border-muted-foreground/40",
-                  )}
-                  aria-hidden="true"
-                />
-              )}
-              <span className="ml-1.5 truncate">{running ? step.activeLabel : step.label}</span>
-              {index < UPDATE_STEPS.length - 1 ? (
-                <span
-                  className={cn(
-                    "mx-2 h-px min-w-3 flex-1",
-                    complete ? "bg-muted-foreground/40" : "bg-border",
-                  )}
-                  aria-hidden="true"
-                />
-              ) : null}
-            </li>
-          );
-        })}
-      </ol>
-      {state.status === "failed" ? (
-        <p className="text-xs text-destructive" role="alert">
+  if (state.status === "failed") {
+    return (
+      <div className="mt-1 flex min-w-0 items-center gap-2 text-xs text-destructive" role="alert">
+        <span className="size-1.5 shrink-0 rounded-full bg-destructive" aria-hidden="true" />
+        <span className="min-w-0 truncate" title={state.message}>
           {state.message}
-        </p>
-      ) : null}
+        </span>
+      </div>
+    );
+  }
+  return (
+    <div className="mt-1 flex items-center gap-2 text-xs font-medium text-foreground">
+      <span
+        className="size-1.5 shrink-0 animate-status-pulse rounded-full bg-foreground"
+        aria-hidden="true"
+      />
+      <span>{serverUpdateStageLabel(state.stage)}</span>
     </div>
   );
 }
@@ -119,7 +72,7 @@ export function ServerUpdateAction({
   serverLabel,
   selfUpdate,
   targetVersion,
-  label = "Update server",
+  label = "Update",
 }: {
   readonly environmentId: EnvironmentId;
   readonly serverLabel: string;
diff --git a/apps/web/src/components/settings/ConnectionsSettings.tsx b/apps/web/src/components/settings/ConnectionsSettings.tsx
index cd3db1a97b1853c607a806caeee27d9a489ab085..35bd6ec65c90f0ec626844551ee6e2144b499f5e 100644
--- a/apps/web/src/components/settings/ConnectionsSettings.tsx
+++ b/apps/web/src/components/settings/ConnectionsSettings.tsx
@@ -4,7 +4,6 @@ import {
   QrCodeIcon,
   RefreshCwIcon,
   TerminalIcon,
-  TriangleAlertIcon,
 } from "lucide-react";
 import { useAtomValue } from "@effect/atom-react";
 import { type ReactNode, memo, useCallback, useId, useMemo, useState } from "react";
@@ -1426,17 +1425,20 @@ function SavedBackendListRow({
           ) : null}
           {serverUpdateState.status !== "idle" ? (
             <div className="max-w-md">
-              <ServerUpdateProgress
-                fromVersion={serverUpdateState.fromVersion}
-                state={serverUpdateState}
-              />
+              <ServerUpdateProgress state={serverUpdateState} />
             </div>
           ) : versionMismatch ? (
-            <p className="flex items-center gap-1 text-warning text-xs">
-              <TriangleAlertIcon className="size-3.5 shrink-0" />
-              Version drift: client {versionMismatch.clientVersion}, server{" "}
-              {versionMismatch.serverVersion}.
-            </p>
+            <Tooltip>
+              <TooltipTrigger
+                render={
+                  <p className="w-fit text-muted-foreground text-xs">Server update available</p>
+                }
+              />
+              <TooltipPopup side="top">
+                {versionMismatch.serverVersion} <span aria-hidden="true">→</span>{" "}
+                {versionMismatch.clientVersion}
+              </TooltipPopup>
+            </Tooltip>
           ) : null}
           {environment.connection.error && !resumingServerUpdate ? (
             <p className="flex min-w-0 items-center gap-2 text-destructive text-xs">
@@ -1461,7 +1463,7 @@ function SavedBackendListRow({
               serverLabel={`${environment.label} server`}
               selfUpdate={resolveServerSelfUpdateCapability(environment.serverConfig)}
               targetVersion={versionMismatch.clientVersion}
-              label={serverUpdateState.status === "failed" ? "Retry update" : "Update server"}
+              label={serverUpdateState.status === "failed" ? "Retry" : "Update"}
             />
           ) : null}
           {isWslEnvironment ? (
@@ -2998,21 +3000,21 @@ export function ConnectionsSettings() {
                     ? "Update failed"
                     : primaryServerUpdateState.status === "running"
                       ? "Updating server"
-                      : "Version drift"
+                      : "Server update available"
                 }
                 description={
                   primaryServerUpdateState.status !== "idle" ? (
-                    <ServerUpdateProgress
-                      fromVersion={primaryServerUpdateState.fromVersion}
-                      state={primaryServerUpdateState}
-                    />
+                    <ServerUpdateProgress state={primaryServerUpdateState} />
                   ) : primaryVersionMismatch ? (
-                    <span className="flex items-center gap-1 text-warning">
-                      <TriangleAlertIcon className="size-3.5 shrink-0" />
-                      Client {primaryVersionMismatch.clientVersion}, server{" "}
-                      {primaryVersionMismatch.serverVersion}. Sync them if RPC calls or reconnects
-                      fail.
-                    </span>
+                    <Tooltip>
+                      <TooltipTrigger
+                        render={<span className="w-fit">Update to match this client.</span>}
+                      />
+                      <TooltipPopup side="top">
+                        {primaryVersionMismatch.serverVersion} <span aria-hidden="true">→</span>{" "}
+                        {primaryVersionMismatch.clientVersion}
+                      </TooltipPopup>
+                    </Tooltip>
                   ) : null
                 }
                 control={
@@ -3024,9 +3026,7 @@ export function ConnectionsSettings() {
                       serverLabel={primaryEnvironment?.label ?? "this server"}
                       selfUpdate={resolveServerSelfUpdateCapability(primaryServerConfig)}
                       targetVersion={primaryVersionMismatch.clientVersion}
-                      {...(primaryServerUpdateState.status === "failed"
-                        ? { label: "Retry update" }
-                        : {})}
+                      label={primaryServerUpdateState.status === "failed" ? "Retry" : "Update"}
                     />
                   ) : undefined
                 }
diff --git a/docs/user/updating.md b/docs/user/updating.md
index ea2ff644cf72186e67d946b066c04b4f72629188..d6c6dfd1c8508b78babcadfb4874c43820e9fee1 100644
--- a/docs/user/updating.md
+++ b/docs/user/updating.md
@@ -35,10 +35,10 @@ An older background-service launcher may ask you to run the exact
 `npx t3@<version> service update` command on the server machine. That one local update installs the
 rollback support needed for later remote updates, including versions that change the database.
 
-After selecting **Update server**, the warning becomes a three-step progress rail:
-**Download**, **Install**, and **Resume**. The same progress appears in the conversation and in
-Connections, so navigating between them does not lose the update. A failed step remains visible
-with its error and an option to retry.
+After selecting **Update**, the notice becomes a live status line: **Downloading…** while the new
+version is fetched and verified, then **Restarting…** while the server restarts into it. The same
+status appears in the conversation and in Connections, so navigating between them does not lose the
+update. A failure remains visible with its error and an option to retry.
 
 **Copy update command** gives you `npx t3@<client-version>`, which relaunches the server directly
 at the matching version. Add whatever startup options you normally use.