diff --git a/apps/web/src/components/sidebar/SidebarUpdatePill.browser.test.tsx b/apps/web/src/components/sidebar/SidebarUpdatePill.browser.test.tsx
index c7b1ca448775c..714d1564bac0a 100644
--- a/apps/web/src/components/sidebar/SidebarUpdatePill.browser.test.tsx
+++ b/apps/web/src/components/sidebar/SidebarUpdatePill.browser.test.tsx
@@ -37,9 +37,10 @@ vi.mock("./useUpdateEverything", () => ({
   useUpdateEverything: () => ({
     hasUpdates: mocks.hasUpdates,
     summary: "Update everything",
-    lines: [],
+    version: null,
+    providerCount: 0,
+    rows: [],
     restarts: [],
-    skipped: [],
   }),
 }));
 
diff --git a/apps/web/src/components/sidebar/SidebarUpdatePill.tsx b/apps/web/src/components/sidebar/SidebarUpdatePill.tsx
index 89c992f8cc9ed..ecfeb4d664a3b 100644
--- a/apps/web/src/components/sidebar/SidebarUpdatePill.tsx
+++ b/apps/web/src/components/sidebar/SidebarUpdatePill.tsx
@@ -396,10 +396,10 @@ function SidebarUpdateControl() {
     <UpdateEverythingDialog
       open={isConfirmingEverything}
       onOpenChange={setIsConfirmingEverything}
-      summary={everything.summary}
-      lines={everything.lines}
+      version={everything.version}
+      providerCount={everything.providerCount}
+      rows={everything.rows}
       restarts={everything.restarts}
-      skipped={everything.skipped}
       onConfirm={() => void runEverything()}
     />
   );
diff --git a/apps/web/src/components/sidebar/UpdateEverythingDialog.tsx b/apps/web/src/components/sidebar/UpdateEverythingDialog.tsx
index e235047d36e1e..8cd5c5ca777d5 100644
--- a/apps/web/src/components/sidebar/UpdateEverythingDialog.tsx
+++ b/apps/web/src/components/sidebar/UpdateEverythingDialog.tsx
@@ -1,6 +1,8 @@
 import { useAtomValue } from "@effect/atom-react";
 import { EnvironmentId } from "@t3tools/contracts";
 import { Atom } from "effect/reactivity";
+import { ChevronRightIcon } from "lucide-react";
+import { Fragment, type RefObject, useRef } from "react";
 
 import { environmentThreadShells } from "~/state/threads";
 import {
@@ -13,7 +15,10 @@ import {
   AlertDialogTitle,
 } from "../ui/alert-dialog";
 import { Button } from "../ui/button";
-import type { RestartingMachine, SkippedMachine } from "./updateEverything.logic";
+import { Collapsible, CollapsiblePanel, CollapsibleTrigger } from "../ui/collapsible";
+import { MiddleTruncate } from "../ui/middle-truncate";
+import { ScrollArea } from "../ui/scroll-area";
+import type { RestartingMachine, UpdateEverythingRow } from "./updateEverything.logic";
 
 const isRunning = (status: string) =>
   status === "preparing" || status === "starting" || status === "running";
@@ -37,35 +42,54 @@ const runningThreadCountAtom = Atom.family((environmentIds: string) =>
 interface UpdateEverythingDialogProps {
   readonly open: boolean;
   readonly onOpenChange: (open: boolean) => void;
-  readonly summary: string;
-  readonly lines: ReadonlyArray<string>;
+  readonly version: string | null;
+  readonly providerCount: number;
+  readonly rows: ReadonlyArray<UpdateEverythingRow>;
   readonly restarts: ReadonlyArray<RestartingMachine>;
-  readonly skipped: ReadonlyArray<SkippedMachine>;
   readonly onConfirm: () => void;
 }
 
+type UpdateEverythingDialogContentProps = Omit<
+  UpdateEverythingDialogProps,
+  "open" | "onOpenChange"
+> & {
+  readonly cancelRef: RefObject<HTMLButtonElement | null>;
+};
+
 export function UpdateEverythingDialog({
   open,
   onOpenChange,
   ...content
 }: UpdateEverythingDialogProps) {
+  const cancelRef = useRef<HTMLButtonElement>(null);
   return (
     <AlertDialog open={open} onOpenChange={onOpenChange}>
       {/* Refocusing the trigger after a pointer close shows its focus ring and opens its tooltip. */}
-      <AlertDialogPopup finalFocus={(closeType) => closeType === "keyboard"}>
-        <UpdateEverythingDialogContent {...content} />
+      <AlertDialogPopup
+        className="sm:max-w-xl"
+        initialFocus={cancelRef}
+        finalFocus={(closeType) => closeType === "keyboard"}
+      >
+        <UpdateEverythingDialogContent {...content} cancelRef={cancelRef} />
       </AlertDialogPopup>
     </AlertDialog>
   );
 }
 
+const APP_LABELS = {
+  "this-app": "This app",
+  server: "Server",
+  "desktop-app": "Desktop app",
+} as const;
+
 function UpdateEverythingDialogContent({
-  summary,
-  lines,
+  version,
+  providerCount,
+  rows,
   restarts,
-  skipped,
   onConfirm,
-}: Omit<UpdateEverythingDialogProps, "open" | "onOpenChange">) {
+  cancelRef,
+}: UpdateEverythingDialogContentProps) {
   const stopped = useAtomValue(
     runningThreadCountAtom(
       restarts
@@ -84,16 +108,96 @@ function UpdateEverythingDialogContent({
   );
   const running = stopped + continuing;
   const threads = `${running} running ${running === 1 ? "thread" : "threads"}`;
+  const restarting = new Set(restarts.map((machine) => machine.environmentId));
+  const updating = rows.filter((row) => row.app !== null || row.providers.length > 0);
+  const skipped = rows.filter((row) => row.skipped !== null);
 
   return (
     <>
-      <AlertDialogHeader>
-        <AlertDialogTitle>{summary}?</AlertDialogTitle>
-        <AlertDialogDescription className="whitespace-pre-line">
-          {lines.join("\n")}
+      <AlertDialogHeader className="shrink-0">
+        <AlertDialogTitle>
+          Update {updating.length} {updating.length === 1 ? "machine" : "machines"}?
+        </AlertDialogTitle>
+        <AlertDialogDescription>
+          {version !== null ? (
+            <>
+              T3 Code <span className="font-mono text-xs">{version}</span>
+            </>
+          ) : null}
+          {version !== null && providerCount > 0 ? " · " : null}
+          {providerCount > 0
+            ? `${providerCount} provider ${providerCount === 1 ? "update" : "updates"}`
+            : null}
         </AlertDialogDescription>
+      </AlertDialogHeader>
+      <ScrollArea scrollFade>
+        <div className="flex flex-col gap-3 px-6 pb-4">
+          {/* Machine names truncate first. Provider lists wrap between names, never inside one. */}
+          <div className="grid grid-cols-[minmax(4rem,max-content)_max-content_minmax(min-content,1fr)_max-content] gap-x-4 text-sm">
+            <div className="col-span-full grid grid-cols-subgrid border-b pb-1.5 text-muted-foreground text-xs">
+              <span>Machine</span>
+              <span>T3 Code</span>
+              <span>Providers</span>
+              <span />
+            </div>
+            {updating.map((row) => (
+              <div
+                key={row.environmentId ?? "this-app"}
+                className="col-span-full grid grid-cols-subgrid border-b border-border/50 py-1.5 last:border-b-0"
+              >
+                <span className="max-w-32 min-w-0">
+                  <MiddleTruncate value={row.label} />
+                </span>
+                <span>
+                  {row.app !== null ? APP_LABELS[row.app] : null}
+                  {row.app === null && row.skipped !== null ? (
+                    <span className="text-muted-foreground">Skipped</span>
+                  ) : null}
+                  {row.app === "this-app" ? (
+                    <span className="block text-muted-foreground text-xs">restarts last</span>
+                  ) : null}
+                </span>
+                <span>
+                  {row.providers.map((provider, index) => (
+                    <Fragment key={provider}>
+                      <span className="whitespace-nowrap">{provider}</span>
+                      {index < row.providers.length - 1 ? ", " : null}
+                    </Fragment>
+                  ))}
+                </span>
+                <span className="text-right">
+                  {row.environmentId !== null && restarting.has(row.environmentId) ? (
+                    <RunningThreads environmentId={row.environmentId} />
+                  ) : null}
+                </span>
+              </div>
+            ))}
+          </div>
+          {skipped.length > 0 ? (
+            <Collapsible>
+              <CollapsibleTrigger className="flex items-center gap-1 text-muted-foreground text-xs hover:text-foreground data-panel-open:[&_svg]:rotate-90">
+                <ChevronRightIcon className="size-3.5 transition-transform" aria-hidden />
+                {skipped.length} skipped
+              </CollapsibleTrigger>
+              <CollapsiblePanel>
+                <div className="grid grid-cols-[minmax(0,max-content)_1fr] gap-x-3 gap-y-0.5 pt-1.5 ps-4.5 text-muted-foreground text-xs">
+                  {skipped.map((row) => (
+                    <Fragment key={row.environmentId ?? "this-app"}>
+                      <span className="max-w-32 min-w-0">
+                        <MiddleTruncate value={row.label} />
+                      </span>
+                      <span className="wrap-anywhere">{row.skipped}</span>
+                    </Fragment>
+                  ))}
+                </div>
+              </CollapsiblePanel>
+            </Collapsible>
+          ) : null}
+        </div>
+      </ScrollArea>
+      <AlertDialogFooter>
         {running > 0 ? (
-          <p className="pt-2 text-sm">
+          <p className="self-center text-muted-foreground text-sm max-sm:order-1 max-sm:text-center sm:mr-auto">
             {stopped === 0
               ? `${threads} will be interrupted and can resume after the restart.`
               : continuing === 0
@@ -101,16 +205,16 @@ function UpdateEverythingDialogContent({
                 : `${threads} will be interrupted. ${continuing} can resume after the restart.`}
           </p>
         ) : null}
-        {skipped.length > 0 ? (
-          <p className="whitespace-pre-line pt-2 text-sm">
-            {skipped.map((machine) => `Skips ${machine.label}: ${machine.reason}`).join("\n")}
-          </p>
-        ) : null}
-      </AlertDialogHeader>
-      <AlertDialogFooter>
-        <AlertDialogClose render={<Button variant="outline" />}>Cancel</AlertDialogClose>
+        <AlertDialogClose ref={cancelRef} render={<Button variant="outline" />}>
+          Cancel
+        </AlertDialogClose>
         <Button onClick={onConfirm}>Update</Button>
       </AlertDialogFooter>
     </>
   );
 }
+
+function RunningThreads({ environmentId }: { readonly environmentId: EnvironmentId }) {
+  const count = useAtomValue(runningThreadCountAtom(environmentId));
+  return count > 0 ? <span className="whitespace-nowrap text-warning">{count} running</span> : null;
+}
diff --git a/apps/web/src/components/sidebar/updateEverything.logic.test.ts b/apps/web/src/components/sidebar/updateEverything.logic.test.ts
index 2bcfd7530b0db..d43bc670a18b6 100644
--- a/apps/web/src/components/sidebar/updateEverything.logic.test.ts
+++ b/apps/web/src/components/sidebar/updateEverything.logic.test.ts
@@ -4,6 +4,7 @@ import { describe, expect, it } from "vite-plus/test";
 import {
   collectRestartingMachines,
   collectServerUpdateTargets,
+  describeUpdateEverything,
   runUpdateEverything,
   type UpdateEverythingMachine,
 } from "./updateEverything.logic";
@@ -142,3 +143,43 @@ describe("runUpdateEverything", () => {
     expect(result.localReady).toBe(false);
   });
 });
+
+describe("describeUpdateEverything", () => {
+  it("gives each machine one row with its T3 Code and provider updates", () => {
+    const id = EnvironmentId.make;
+    const { rows } = describeUpdateEverything({
+      localVersion: "1.1.0",
+      localMachines: [
+        { environmentId: id("local"), label: "Mainbook" },
+        { environmentId: id("wsl"), label: "Mainbook WSL" },
+      ],
+      servers: [
+        {
+          environmentId: id("npm"),
+          serverLabel: "bb-1",
+          selfUpdate: "respawn",
+          targetVersion: "1.1.0",
+        },
+      ],
+      providerMachines: [
+        { environmentId: id("npm"), label: "bb-1", providers: ["Codex", "Claude"] },
+        { environmentId: id("local"), label: "Mainbook", providers: ["Codex"] },
+        { environmentId: id("manual"), label: "alvin", providers: ["Claude"] },
+      ],
+      skipped: [
+        { environmentId: id("manual"), label: "alvin", reason: "needs a manual update" },
+        { environmentId: id("offline"), label: "TheoRoom", reason: "not connected" },
+      ],
+    });
+
+    expect(
+      rows.map(({ label, app, skipped, providers }) => [label, app, skipped, providers]),
+    ).toEqual([
+      ["Mainbook", "this-app", null, ["Codex"]],
+      ["Mainbook WSL", "this-app", null, []],
+      ["bb-1", "server", null, ["Codex", "Claude"]],
+      ["alvin", null, "needs a manual update", ["Claude"]],
+      ["TheoRoom", null, "not connected", []],
+    ]);
+  });
+});
diff --git a/apps/web/src/components/sidebar/updateEverything.logic.ts b/apps/web/src/components/sidebar/updateEverything.logic.ts
index d4fb711dfe6ab..71247b6214028 100644
--- a/apps/web/src/components/sidebar/updateEverything.logic.ts
+++ b/apps/web/src/components/sidebar/updateEverything.logic.ts
@@ -356,6 +356,11 @@ export function getUpdateEverythingToastView(
 
 export interface UpdateEverythingPlan {
   readonly localVersion: string | null;
+  /** Machines whose servers this app hosts; this app's update restarts them. */
+  readonly localMachines: ReadonlyArray<{
+    readonly environmentId: EnvironmentId;
+    readonly label: string;
+  }>;
   readonly servers: ReadonlyArray<
     Pick<ServerUpdateTarget, "environmentId" | "serverLabel" | "selfUpdate" | "targetVersion">
   >;
@@ -364,6 +369,15 @@ export interface UpdateEverythingPlan {
     readonly label: string;
     readonly providers: ReadonlyArray<string>;
   }>;
+  readonly skipped: ReadonlyArray<SkippedMachine>;
+}
+
+export interface UpdateEverythingRow {
+  readonly environmentId: EnvironmentId | null;
+  readonly label: string;
+  readonly app: "this-app" | "server" | "desktop-app" | null;
+  readonly skipped: string | null;
+  readonly providers: ReadonlyArray<string>;
 }
 
 function countLabel(count: number, noun: string): string | null {
@@ -375,9 +389,12 @@ function joinList(parts: ReadonlyArray<string>): string {
   return `${parts.slice(0, -1).join(", ")}, and ${parts.at(-1)}`;
 }
 
+/** One row per machine: this app's machines first, then servers, provider-only, and skipped. */
 export function describeUpdateEverything(plan: UpdateEverythingPlan): {
   readonly summary: string;
-  readonly lines: ReadonlyArray<string>;
+  readonly version: string | null;
+  readonly providerCount: number;
+  readonly rows: ReadonlyArray<UpdateEverythingRow>;
 } {
   const providerCount = plan.providerMachines.reduce(
     (count, machine) => count + machine.providers.length,
@@ -391,30 +408,46 @@ export function describeUpdateEverything(plan: UpdateEverythingPlan): {
     ].filter((part) => part !== null),
   )}`;
 
-  const machines = new Map<EnvironmentId, { label: string; items: string[] }>();
-  const itemsFor = (environmentId: EnvironmentId, label: string) => {
-    const existing = machines.get(environmentId);
-    if (existing) return existing.items;
-    const items: string[] = [];
-    machines.set(environmentId, { label, items });
-    return items;
+  const rows = new Map<EnvironmentId | null, UpdateEverythingRow>();
+  const update = (
+    environmentId: EnvironmentId | null,
+    label: string,
+    change: Partial<UpdateEverythingRow>,
+  ) => {
+    const row = rows.get(environmentId) ?? {
+      environmentId,
+      label,
+      app: null,
+      skipped: null,
+      providers: [],
+    };
+    rows.set(environmentId, { ...row, ...change });
   };
+  if (plan.localVersion) {
+    if (plan.localMachines.length === 0) update(null, "This app", { app: "this-app" });
+    for (const machine of plan.localMachines) {
+      update(machine.environmentId, machine.label, { app: "this-app" });
+    }
+  }
   for (const server of plan.servers) {
-    itemsFor(server.environmentId, server.serverLabel).push(
-      server.selfUpdate === "desktop-managed"
-        ? "desktop app update"
-        : `server to ${server.targetVersion}`,
-    );
+    update(server.environmentId, server.serverLabel, {
+      app: server.selfUpdate === "desktop-managed" ? "desktop-app" : "server",
+    });
   }
   for (const machine of plan.providerMachines) {
-    itemsFor(machine.environmentId, machine.label).push(...machine.providers);
+    update(machine.environmentId, machine.label, { providers: machine.providers });
+  }
+  for (const machine of plan.skipped) {
+    update(machine.environmentId, machine.label, { skipped: machine.reason });
   }
 
   return {
     summary,
-    lines: [
-      ...(plan.localVersion ? [`This app: ${plan.localVersion}, restarts last`] : []),
-      ...Array.from(machines.values(), ({ label, items }) => `${label}: ${items.join(", ")}`),
-    ],
+    version:
+      plan.localVersion ??
+      plan.servers.find((server) => server.selfUpdate !== "desktop-managed")?.targetVersion ??
+      null,
+    providerCount,
+    rows: Array.from(rows.values()),
   };
 }
diff --git a/apps/web/src/components/sidebar/useUpdateEverything.ts b/apps/web/src/components/sidebar/useUpdateEverything.ts
index e9e5a9b78efc6..af38bbf5d4bc4 100644
--- a/apps/web/src/components/sidebar/useUpdateEverything.ts
+++ b/apps/web/src/components/sidebar/useUpdateEverything.ts
@@ -78,9 +78,11 @@ export function useUpdateEverything(localUpdateVersion: string | null) {
   const providers = useProviderUpdates();
   const updateServer = useServerUpdate();
 
-  const { summary, lines } = describeUpdateEverything({
+  const view = describeUpdateEverything({
     localVersion: localUpdateVersion,
+    localMachines: machines.filter((machine) => machine.hostedByThisApp),
     servers,
+    skipped,
     providerMachines: providers.machines.map((machine) => ({
       environmentId: machine.environmentId,
       label: machine.label,
@@ -92,10 +94,8 @@ export function useUpdateEverything(localUpdateVersion: string | null) {
 
   return {
     hasUpdates: servers.length > 0 || providers.machines.length > 0,
-    summary,
-    lines,
+    ...view,
     restarts,
-    skipped,
     run: async ({
       downloadLocal,
       installLocal,