diff --git a/apps/web/src/components/sidebar/DesktopUpdateStatusIcon.tsx b/apps/web/src/components/sidebar/DesktopUpdateStatusIcon.tsx
new file mode 100644
index 00000000000..9346a742a37
--- /dev/null
+++ b/apps/web/src/components/sidebar/DesktopUpdateStatusIcon.tsx
@@ -0,0 +1,126 @@
+import { CheckIcon, DownloadIcon, RefreshCwIcon, RotateCwIcon } from "lucide-react";
+import type { AnimationEventHandler } from "react";
+
+import { cn } from "../../lib/utils";
+
+const DOWNLOAD_PROGRESS_RADIUS = 14;
+const DOWNLOAD_PROGRESS_CIRCUMFERENCE = 2 * Math.PI * DOWNLOAD_PROGRESS_RADIUS;
+
+export type DesktopUpdateStatusIconState =
+  | "idle"
+  | "checking"
+  | "available"
+  | "downloading"
+  | "downloaded";
+
+function normalizeDesktopUpdateDownloadPercent(percent: number | null): number {
+  if (percent === null || !Number.isFinite(percent)) return 0;
+  return Math.min(100, Math.max(0, percent));
+}
+
+export function shouldShowDesktopUpdateCheckIcon({
+  isAnimationLatched,
+  isChecking,
+  prefersReducedMotion,
+}: {
+  readonly isAnimationLatched: boolean;
+  readonly isChecking: boolean;
+  readonly prefersReducedMotion: boolean;
+}): boolean {
+  return isChecking || (isAnimationLatched && !prefersReducedMotion);
+}
+
+export function shouldContinueDesktopUpdateCheckAnimation({
+  isChecking,
+  prefersReducedMotion,
+}: {
+  readonly isChecking: boolean;
+  readonly prefersReducedMotion: boolean;
+}): boolean {
+  return isChecking && !prefersReducedMotion;
+}
+
+function DesktopUpdateAvailableIcon() {
+  return (
+    <span className="relative grid size-4 place-items-center">
+      <DownloadIcon className="size-4" />
+      <span
+        aria-hidden="true"
+        className="absolute -top-0.5 -right-0.5 size-1.5 rounded-full bg-update-foreground ring-2 ring-update-surface"
+      />
+    </span>
+  );
+}
+
+function DesktopUpdateDownloadingIcon({ percent }: { readonly percent: number | null }) {
+  const normalizedPercent = normalizeDesktopUpdateDownloadPercent(percent);
+  const progressOffset = DOWNLOAD_PROGRESS_CIRCUMFERENCE * (1 - normalizedPercent / 100);
+
+  return (
+    <span className="relative grid size-8 place-items-center">
+      <svg
+        aria-hidden="true"
+        className="pointer-events-none absolute inset-0 size-full -rotate-90"
+        viewBox="0 0 32 32"
+      >
+        <circle
+          cx="16"
+          cy="16"
+          r={DOWNLOAD_PROGRESS_RADIUS}
+          fill="none"
+          stroke="color-mix(in srgb, currentColor 22%, transparent)"
+          strokeWidth="1.5"
+        />
+        <circle
+          cx="16"
+          cy="16"
+          r={DOWNLOAD_PROGRESS_RADIUS}
+          fill="none"
+          stroke="currentColor"
+          strokeDasharray={DOWNLOAD_PROGRESS_CIRCUMFERENCE}
+          strokeDashoffset={progressOffset}
+          strokeLinecap="round"
+          strokeWidth="1.5"
+          className="transition-[stroke-dashoffset] duration-300 ease-out motion-reduce:transition-none"
+        />
+      </svg>
+      <DownloadIcon className="size-4" />
+    </span>
+  );
+}
+
+function DesktopUpdateDownloadedIcon() {
+  return (
+    <span className="relative grid size-4 place-items-center">
+      <RotateCwIcon className="size-4" />
+      <span className="absolute -right-1 -bottom-1 grid size-2.5 place-items-center rounded-full bg-update-foreground text-background ring-2 ring-background">
+        <CheckIcon className="size-2" strokeWidth={3} />
+      </span>
+    </span>
+  );
+}
+
+export function DesktopUpdateStatusIcon({
+  downloadPercent,
+  isCheckAnimating,
+  onCheckAnimationIteration,
+  status,
+}: {
+  readonly downloadPercent?: number | null;
+  readonly isCheckAnimating?: boolean;
+  readonly onCheckAnimationIteration?: AnimationEventHandler<SVGSVGElement>;
+  readonly status: DesktopUpdateStatusIconState;
+}) {
+  if (status === "available") return <DesktopUpdateAvailableIcon />;
+  if (status === "downloading") {
+    return <DesktopUpdateDownloadingIcon percent={downloadPercent ?? null} />;
+  }
+  if (status === "downloaded") return <DesktopUpdateDownloadedIcon />;
+
+  return (
+    <RefreshCwIcon
+      className={cn("size-4", status === "checking" && isCheckAnimating && "animate-spin")}
+      onAnimationIteration={onCheckAnimationIteration}
+    />
+  );
+}
diff --git a/apps/web/src/components/sidebar/SidebarUpdatePill.tsx b/apps/web/src/components/sidebar/SidebarUpdatePill.tsx
index 191f30438dd..c5cffd8110b 100644
--- a/apps/web/src/components/sidebar/SidebarUpdatePill.tsx
+++ b/apps/web/src/components/sidebar/SidebarUpdatePill.tsx
@@ -1,6 +1,7 @@
-import { DownloadIcon, RefreshCwIcon, RotateCwIcon, TriangleAlertIcon } from "lucide-react";
-import { useCallback, useState } from "react";
+import { TriangleAlertIcon } from "lucide-react";
+import { useCallback, useEffect, useState } from "react";
 import { isElectron } from "../../env";
+import { useMediaQuery } from "../../hooks/useMediaQuery";
 import { cn } from "../../lib/utils";
 import { ensureLocalApi } from "../../localApi";
 import { useDesktopUpdateState } from "../../state/desktopUpdate";
@@ -21,6 +22,38 @@ import { Alert, AlertDescription, AlertTitle } from "../ui/alert";
 import { Separator } from "../ui/separator";
 import { SidebarMenuItem } from "../ui/sidebar";
 import { Tooltip, TooltipPopup, TooltipTrigger } from "../ui/tooltip";
+import {
+  DesktopUpdateStatusIcon,
+  shouldContinueDesktopUpdateCheckAnimation,
+  shouldShowDesktopUpdateCheckIcon,
+} from "./DesktopUpdateStatusIcon";
+
+function resolveSidebarUpdatePresentation({
+  action,
+  isDownloading,
+  showCheckIcon,
+}: {
+  readonly action: ReturnType<typeof resolveDesktopUpdateButtonAction>;
+  readonly isDownloading: boolean;
+  readonly showCheckIcon: boolean;
+}) {
+  const showUpdateDetails = action !== "none" || isDownloading;
+  const iconStatus = showCheckIcon
+    ? "checking"
+    : action === "install"
+      ? "downloaded"
+      : isDownloading
+        ? "downloading"
+        : action === "download"
+          ? "available"
+          : "idle";
+
+  return {
+    iconStatus,
+    showUpdateDetails,
+    showUpdateIconState: showUpdateDetails && !showCheckIcon,
+  } as const;
+}
 
 function keyReleaseNoteItems(items: ReadonlyArray<string>) {
   const occurrences = new Map<string, number>();
@@ -110,18 +143,42 @@ export function SidebarUpdatePill() {
 function SidebarUpdateControl() {
   const state = useDesktopUpdateState();
   const [isActionPending, setIsActionPending] = useState(false);
+  const [checkAnimationKey, setCheckAnimationKey] = useState(0);
+  const [isCheckAnimationLatched, setIsCheckAnimationLatched] = useState(false);
+  const prefersReducedMotion = useMediaQuery("(prefers-reduced-motion: reduce)");
+
+  useEffect(() => {
+    if (prefersReducedMotion) {
+      setIsCheckAnimationLatched(false);
+    } else if (state?.status === "checking") {
+      setIsCheckAnimationLatched(true);
+    }
+  }, [prefersReducedMotion, state?.status]);
 
   const action = state ? resolveDesktopUpdateButtonAction(state) : "none";
   const isDownloading = state?.status === "downloading";
-  const isUpdateState = action !== "none" || isDownloading;
-  const tooltip = isUpdateState
+  const showCheckIcon = shouldShowDesktopUpdateCheckIcon({
+    isAnimationLatched: isCheckAnimationLatched,
+    isChecking: state?.status === "checking",
+    prefersReducedMotion,
+  });
+  const { iconStatus, showUpdateDetails, showUpdateIconState } = resolveSidebarUpdatePresentation({
+    action,
+    isDownloading,
+    showCheckIcon,
+  });
+  const tooltip = showUpdateDetails
     ? state
       ? getDesktopUpdateButtonTooltip(state)
       : "Update available"
-    : state?.status === "checking"
+    : showCheckIcon
       ? "Checking for updates…"
       : "Check for updates";
-  const disabled = isUpdateState ? isDesktopUpdateButtonDisabled(state) : !canCheckForUpdate(state);
+  const disabled = showCheckIcon
+    ? true
+    : showUpdateDetails
+      ? isDesktopUpdateButtonDisabled(state)
+      : !canCheckForUpdate(state);
 
   const handleAction = useCallback(async () => {
     const bridge = window.desktopBridge;
@@ -209,6 +266,10 @@ function SidebarUpdateControl() {
       return;
     }
 
+    if (!prefersReducedMotion) {
+      setIsCheckAnimationLatched(true);
+      setCheckAnimationKey((key) => key + 1);
+    }
     void bridge
       .checkForUpdate()
       .then((result) => {
@@ -232,7 +293,16 @@ function SidebarUpdateControl() {
         );
       })
       .finally(() => setIsActionPending(false));
-  }, [action, disabled, isActionPending, state]);
+  }, [action, disabled, isActionPending, prefersReducedMotion, state]);
+
+  const handleCheckAnimationIteration = useCallback(() => {
+    setIsCheckAnimationLatched(
+      shouldContinueDesktopUpdateCheckAnimation({
+        isChecking: state?.status === "checking",
+        prefersReducedMotion,
+      }),
+    );
+  }, [prefersReducedMotion, state?.status]);
 
   return (
     <SidebarMenuItem className="ml-auto shrink-0">
@@ -245,29 +315,28 @@ function SidebarUpdateControl() {
               aria-disabled={disabled || isActionPending || undefined}
               disabled={disabled || isActionPending}
               className={cn(
-                "inline-flex size-8 items-center justify-center rounded-full outline-hidden ring-ring transition-colors enabled:cursor-pointer focus-visible:ring-2 disabled:cursor-not-allowed disabled:opacity-60",
-                isUpdateState
+                "inline-flex size-8 items-center justify-center rounded-full outline-hidden ring-ring transition-colors enabled:cursor-pointer focus-visible:ring-2 disabled:cursor-not-allowed",
+                showUpdateIconState
                   ? "bg-update-surface text-update-foreground enabled:hover:bg-update/12"
                   : "text-[var(--sidebar-icon-color)] enabled:hover:bg-sidebar-row-hover enabled:hover:text-sidebar-foreground",
+                disabled && !showUpdateIconState && "opacity-60",
               )}
               onClick={handleAction}
             >
-              {action === "install" ? (
-                <RotateCwIcon className="size-4" />
-              ) : isUpdateState ? (
-                <DownloadIcon className="size-4" />
-              ) : (
-                <RefreshCwIcon
-                  className={cn("size-4", state?.status === "checking" && "animate-spin")}
-                />
-              )}
+              <DesktopUpdateStatusIcon
+                key={showCheckIcon ? checkAnimationKey : iconStatus}
+                downloadPercent={state?.downloadPercent ?? null}
+                isCheckAnimating={showCheckIcon && !prefersReducedMotion}
+                onCheckAnimationIteration={handleCheckAnimationIteration}
+                status={iconStatus}
+              />
             </button>
           }
         />
         <TooltipPopup
           align="center"
           className={
-            isUpdateState && state?.channel === "nightly" && state.releaseNotes.length > 0
+            showUpdateDetails && state?.channel === "nightly" && state.releaseNotes.length > 0
               ? // pointer-events-auto overrides the positioner's pointer-events-none so the
                 // release notes stay open (and scrollable) when the cursor moves into them.
                 "pointer-events-auto max-w-none text-balance"
@@ -275,7 +344,7 @@ function SidebarUpdateControl() {
           }
           side="top"
           style={
-            isUpdateState
+            showUpdateDetails
               ? {
                   background:
                     "color-mix(in srgb, var(--update) 18%, color-mix(in srgb, var(--popover) var(--glass-opacity), transparent))",
@@ -283,9 +352,9 @@ function SidebarUpdateControl() {
                 }
               : undefined
           }
-          variant={isUpdateState ? "glass" : "default"}
+          variant={showUpdateDetails ? "glass" : "default"}
         >
-          {isUpdateState && state ? (
+          {showUpdateDetails && state ? (
             <SidebarUpdateReleaseNotesTooltip state={state} tooltip={tooltip} />
           ) : (
             tooltip