SwitchbackTech · tyler-dane · Aug 1, 2026 · Aug 1, 2026
diff --git a/packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.util.test.ts b/packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.util.test.ts
@@ -16,19 +16,19 @@ describe("formatLastSyncedLabel", () => {
 
   it("formats recent relative ages", () => {
     expect(formatLastSyncedLabel("2026-07-24T11:59:30.000Z", nowMs)).toBe(
-      "Last synced just now",
+      "Updated just now",
     );
     expect(formatLastSyncedLabel("2026-07-24T11:59:00.000Z", nowMs)).toBe(
-      "Last synced 1 minute ago",
+      "Updated 1 minute ago",
     );
     expect(formatLastSyncedLabel("2026-07-24T11:45:00.000Z", nowMs)).toBe(
-      "Last synced 15 minutes ago",
+      "Updated 15 minutes ago",
     );
     expect(formatLastSyncedLabel("2026-07-24T10:00:00.000Z", nowMs)).toBe(
-      "Last synced 2 hours ago",
+      "Updated 2 hours ago",
     );
     expect(formatLastSyncedLabel("2026-07-22T12:00:00.000Z", nowMs)).toBe(
-      "Last synced 2 days ago",
+      "Updated 2 days ago",
     );
   });
 });
@@ -41,25 +41,22 @@ describe("getGoogleSyncStatus", () => {
   it("returns healthy copy for connected Google", () => {
     expect(getGoogleSyncStatus("HEALTHY")).toEqual({
       variant: "healthy",
-      text: "Calendar up-to-date",
+      text: "Calendar connected",
     });
   });
 
-  it("returns checking copy while metadata loads", () => {
-    expect(getGoogleSyncStatus("checking")).toEqual({
-      variant: "syncing",
-      text: "Checking calendar status…",
-    });
+  it("hides transient metadata loading without a connection summary", () => {
+    expect(getGoogleSyncStatus("checking")).toBeNull();
   });
 
-  it("returns syncing copy while importing", () => {
+  it("uses setup copy while importing", () => {
     expect(getGoogleSyncStatus("IMPORTING")).toEqual({
       variant: "syncing",
-      text: "Syncing your calendar…",
+      text: "Adding your calendar…",
     });
   });
 
-  it("shows checking progress over a cached healthy connection", () => {
+  it("keeps a cached healthy connection calm while metadata loads", () => {
     expect(
       getGoogleSyncStatus("checking", {
         id: "c1",
@@ -70,12 +67,12 @@ describe("getGoogleSyncStatus", () => {
         accountEmail: "a@example.com",
       }),
     ).toEqual({
-      variant: "syncing",
-      text: "Checking calendar status…",
+      variant: "healthy",
+      text: "Calendar connected",
     });
   });
 
-  it("shows import progress over a cached healthy connection", () => {
+  it("keeps a cached healthy connection calm during a routine refresh", () => {
     expect(
       getGoogleSyncStatus("IMPORTING", {
         id: "c1",
@@ -86,24 +83,25 @@ describe("getGoogleSyncStatus", () => {
         accountEmail: "a@example.com",
       }),
     ).toEqual({
-      variant: "syncing",
-      text: "Syncing your calendar…",
+      variant: "healthy",
+      text: "Calendar connected",
     });
   });
 
   it("returns warning copy for ATTENTION, without using the word 'repair'", () => {
     const status = getGoogleSyncStatus("ATTENTION");
 
     expect(status?.variant).toBe("warning");
-    expect(status?.text.toLowerCase()).not.toContain("repair");
-    expect(status?.text.toLowerCase()).toContain("refresh");
+    expect(status?.text).toBe(
+      "Calendar updates are taking longer than usual. We'll keep trying.",
+    );
   });
 
   it("returns error copy for RECONNECT_REQUIRED", () => {
     expect(getGoogleSyncStatus("RECONNECT_REQUIRED")?.variant).toBe("error");
   });
 
-  it("uses the same syncing copy for every in-progress Sync state", () => {
+  it("shows setup copy for a connection that has never been healthy", () => {
     expect(
       getGoogleSyncStatus("IMPORTING", {
         id: "c1",
@@ -115,7 +113,7 @@ describe("getGoogleSyncStatus", () => {
       }),
     ).toEqual({
       variant: "syncing",
-      text: "Syncing your calendar…",
+      text: "Adding your calendar…",
     });
   });
 
@@ -131,7 +129,7 @@ describe("getGoogleSyncStatus", () => {
       }),
     ).toEqual({
       variant: "warning",
-      text: "Calendar sync is delayed — try Refresh",
+      text: "Calendar updates are taking longer than usual. We'll keep trying.",
     });
   });
 
@@ -147,7 +145,7 @@ describe("getGoogleSyncStatus", () => {
       }),
     ).toEqual({
       variant: "healthy",
-      text: "Calendar up-to-date",
+      text: "Calendar connected",
     });
   });
 });

diff --git a/packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.util.ts b/packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.util.ts
@@ -9,6 +9,14 @@ import {
 
 const CONNECT_ICON: CommandActionIcon = CloudArrowUpIcon;
 const REFRESH_ICON: CommandActionIcon = ArrowsClockwiseIcon;
+const CONNECTED_STATUS: SyncStatus = {
+  variant: "healthy",
+  text: "Calendar connected",
+};
+const DELAYED_STATUS: SyncStatus = {
+  variant: "warning",
+  text: "Calendar updates are taking longer than usual. We'll keep trying.",
+};
 
 /** Short relative label for Sync connection `lastSyncedAt` (ISO). */
 export const formatLastSyncedLabel = (
@@ -26,31 +34,31 @@ export const formatLastSyncedLabel = (
 
   const deltaSec = Math.max(0, Math.floor((nowMs - syncedMs) / 1000));
   if (deltaSec < 60) {
-    return "Last synced just now";
+    return "Updated just now";
   }
 
   const deltaMin = Math.floor(deltaSec / 60);
   if (deltaMin < 60) {
     return deltaMin === 1
-      ? "Last synced 1 minute ago"
-      : `Last synced ${deltaMin} minutes ago`;
+      ? "Updated 1 minute ago"
+      : `Updated ${deltaMin} minutes ago`;
   }
 
   const deltaHr = Math.floor(deltaMin / 60);
   if (deltaHr < 24) {
     return deltaHr === 1
-      ? "Last synced 1 hour ago"
-      : `Last synced ${deltaHr} hours ago`;
+      ? "Updated 1 hour ago"
+      : `Updated ${deltaHr} hours ago`;
   }
 
   const deltaDay = Math.floor(deltaHr / 24);
   if (deltaDay < 7) {
     return deltaDay === 1
-      ? "Last synced 1 day ago"
-      : `Last synced ${deltaDay} days ago`;
+      ? "Updated 1 day ago"
+      : `Updated ${deltaDay} days ago`;
   }
 
-  return `Last synced ${new Date(syncedMs).toLocaleDateString()}`;
+  return `Updated ${new Date(syncedMs).toLocaleDateString()}`;
 };
 
 export type GoogleConnectionHandlers = {
@@ -102,29 +110,21 @@ export const getGoogleSyncStatus = (
   state: GoogleUiState,
   connection?: GoogleSyncConnectionSummary | null,
 ): SyncStatus => {
-  // Local transient states are newer than a cached server summary, which can
-  // still report healthy while a fresh check or import is underway.
-  if (state === "checking") {
-    return { variant: "syncing", text: "Checking calendar status…" };
-  }
-
-  if (state === "IMPORTING") {
-    return { variant: "syncing", text: "Syncing your calendar…" };
-  }
-
+  // A connection summary describes durable provider work. Local metadata
+  // loading and a routine incremental pull must not replace a calm, usable
+  // calendar with transient "checking" or "syncing" copy.
   if (connection) {
     switch (connection.state) {
       case "healthy":
-        return { variant: "healthy", text: "Calendar up-to-date" };
+        return CONNECTED_STATUS;
       case "connecting":
       case "importing":
       case "catchingUp":
-        return { variant: "syncing", text: "Syncing your calendar…" };
+        return connection.lastHealthyAt
+          ? CONNECTED_STATUS
+          : { variant: "syncing", text: "Adding your calendar…" };
       case "delayed":
-        return {
-          variant: "warning",
-          text: "Calendar sync is delayed — try Refresh",
-        };
+        return DELAYED_STATUS;
       case "actionRequired":
       case "disconnected":
         // Product enum already distinguishes reconnect vs soft attention.
@@ -133,13 +133,14 @@ export const getGoogleSyncStatus = (
   }
 
   switch (state) {
+    case "checking":
+      return null;
+    case "IMPORTING":
+      return { variant: "syncing", text: "Adding your calendar…" };
     case "HEALTHY":
-      return { variant: "healthy", text: "Calendar up-to-date" };
+      return CONNECTED_STATUS;
     case "ATTENTION":
-      return {
-        variant: "warning",
-        text: "Calendar needs a refresh",
-      };
+      return DELAYED_STATUS;
     case "RECONNECT_REQUIRED":
       return { variant: "error", text: "Calendar needs reconnecting" };
     case "NOT_CONNECTED":

diff --git a/packages/web/src/components/Sidebar/CalendarList/CalendarListHeader.test.tsx b/packages/web/src/components/Sidebar/CalendarList/CalendarListHeader.test.tsx
@@ -194,8 +194,8 @@ describe("CalendarListHeader", () => {
     expect(email.tagName).toBe("SPAN");
     expect(email).toHaveClass("text-text");
     expect(email).not.toHaveClass("c-sync-text-wave");
-    expect(screen.getByRole("status")).toHaveTextContent("Calendar up-to-date");
-    expect(screen.queryByText(/Last synced/)).toBeNull();
+    expect(screen.getByRole("status")).toHaveTextContent("Calendar connected");
+    expect(screen.queryByText(/Updated/)).toBeNull();
 
     await user.hover(email);
     expect(screen.queryByRole("tooltip")).toBeNull();
@@ -220,26 +220,25 @@ describe("CalendarListHeader", () => {
 
     renderHeader();
 
-    expect(screen.getByRole("status")).toHaveTextContent("Calendar up-to-date");
-    expect(screen.getByText("Last synced just now")).toBeInTheDocument();
+    expect(screen.getByRole("status")).toHaveTextContent("Calendar connected");
+    expect(screen.getByText("Updated just now")).toBeInTheDocument();
     expect(
       screen.queryByRole("button", { name: /Google Calendar/ }),
     ).toBeNull();
   });
 
-  it.each([
-    ["IMPORTING", "Syncing your calendar…"],
-    ["checking", "Checking calendar status…"],
-  ] as const)("shows the visible %s status for %s", async (state, status) => {
+  it("shows setup status only while the first calendar import is in progress", async () => {
     const user = userEvent.setup();
     mockEmail = "ahab@pequod.com";
-    mockGoogleState = state;
+    mockGoogleState = "IMPORTING";
 
     renderHeader();
 
     const email = screen.getByText("ahab@pequod.com");
     expect(email).toHaveClass("c-sync-text-wave");
-    expect(screen.getByRole("status")).toHaveTextContent(status);
+    expect(screen.getByRole("status")).toHaveTextContent(
+      "Adding your calendar…",
+    );
 
     await user.hover(email);
     expect(screen.queryByRole("tooltip")).toBeNull();
@@ -257,7 +256,7 @@ describe("CalendarListHeader", () => {
     expect(email).toHaveClass("text-text");
     expect(email).not.toHaveClass("text-warning");
     expect(screen.getByRole("status")).toHaveTextContent(
-      "Calendar needs a refresh",
+      "Calendar updates are taking longer than usual. We'll keep trying.",
     );
     expect(screen.getByRole("status")).toHaveClass("text-warning");
 
@@ -340,7 +339,7 @@ describe("CalendarListHeader", () => {
       name: "Refreshing…",
     });
     expect(screen.getByRole("status")).toHaveTextContent(
-      "Requesting a calendar refresh…",
+      "Calendar updates are taking longer than usual. We'll keep trying.",
     );
     expect(refreshButton).toBeDisabled();
     expect(refreshButton).toHaveAttribute("aria-busy", "true");
@@ -379,7 +378,7 @@ describe("CalendarListHeader", () => {
     );
   });
 
-  it("uses the same syncing copy for an in-progress reconciliation", () => {
+  it("keeps an established calendar calm during reconciliation", () => {
     mockEmail = "ahab@pequod.com";
     mockGoogleState = "HEALTHY";
     userMetadataActions.set({
@@ -398,10 +397,8 @@ describe("CalendarListHeader", () => {
 
     renderHeader();
 
-    expect(screen.getByRole("status")).toHaveTextContent(
-      "Syncing your calendar…",
-    );
-    expect(screen.queryByText("Catching up your calendar…")).toBeNull();
-    expect(screen.queryByText(/Last synced/)).toBeNull();
+    expect(screen.getByRole("status")).toHaveTextContent("Calendar connected");
+    expect(screen.queryByText("Adding your calendar…")).toBeNull();
+    expect(screen.getByText("Updated just now")).toBeInTheDocument();
   });
 });
diff --git a/packages/web/src/components/Sidebar/CalendarList/CalendarListHeader.tsx b/packages/web/src/components/Sidebar/CalendarList/CalendarListHeader.tsx
@@ -52,13 +52,11 @@ const getSidebarSyncStatus = ({
   googleStatus,
   hasPendingEventMutations,
   isConnecting,
-  isRefreshing,
   state,
 }: {
   googleStatus: SyncStatus;
   hasPendingEventMutations: boolean;
   isConnecting: boolean;
-  isRefreshing: boolean;
   state: GoogleUiState;
 }): SyncStatus => {
   if (isConnecting) {
@@ -71,10 +69,6 @@ const getSidebarSyncStatus = ({
     };
   }
 
-  if (isRefreshing) {
-    return { variant: "syncing", text: "Requesting a calendar refresh…" };
-  }
-
   if (googleStatus && googleStatus.variant !== "healthy") {
     return googleStatus;
   }
@@ -154,7 +148,6 @@ const AuthenticatedAccountHeader: FC<{ email: string }> = ({ email }) => {
     googleStatus: getGoogleSyncStatus(state, syncConnection),
     hasPendingEventMutations,
     isConnecting,
-    isRefreshing,
     state,
   });
   const isSyncing =

diff --git a/packages/web/src/sse/hooks/useSyncFocusRefresh.test.ts b/packages/web/src/sse/hooks/useSyncFocusRefresh.test.ts
@@ -94,6 +94,21 @@ describe("useSyncFocusRefresh", () => {
     expect(refresh).toHaveBeenCalledTimes(1);
   });
 
+  it("does not retrigger after the refresh changes connection state", () => {
+    const refresh = mock();
+    let state: UseConnectGoogleResult["state"] = "HEALTHY";
+    const hook = renderHook(() =>
+      useSyncFocusRefresh(() => fakeConnectGoogle({ refresh, state })),
+    );
+
+    state = "IMPORTING";
+    hook.rerender();
+    state = "HEALTHY";
+    hook.rerender();
+
+    expect(refresh).toHaveBeenCalledTimes(1);
+  });
+
   it("refreshes again when the tab regains focus after being hidden long enough", () => {
     setSystemTime(new Date("2026-02-05T00:00:00.000Z"));
     const refresh = mock();