diff --git a/e2e/garmin.spec.ts b/e2e/garmin.spec.ts
new file mode 100644
index 0000000..88a55a2
--- /dev/null
+++ b/e2e/garmin.spec.ts
@@ -0,0 +1,191 @@
+// ABOUTME: E2E tests for Garmin token connection flow.
+// ABOUTME: Tests saving tokens, verifying connection status, and disconnection.
+import { expect, test } from "@playwright/test";
+
+test.describe("garmin connection", () => {
+  test.describe("unauthenticated", () => {
+    test("redirects to login when not authenticated", async ({ page }) => {
+      await page.goto("/settings/garmin");
+      await expect(page).toHaveURL(/\/login/);
+    });
+  });
+
+  test.describe("authenticated", () => {
+    test.beforeEach(async ({ page }) => {
+      const email = process.env.TEST_USER_EMAIL;
+      const password = process.env.TEST_USER_PASSWORD;
+
+      if (!email || !password) {
+        test.skip();
+        return;
+      }
+
+      // Login via the login page
+      await page.goto("/login");
+      await page.waitForLoadState("networkidle");
+
+      const emailInput = page.getByLabel(/email/i);
+      const hasEmailForm = await emailInput.isVisible().catch(() => false);
+
+      if (!hasEmailForm) {
+        test.skip();
+        return;
+      }
+
+      await emailInput.fill(email);
+      await page.getByLabel(/password/i).fill(password);
+      await page.getByRole("button", { name: /sign in/i }).click();
+
+      // Wait for redirect to dashboard, then navigate to garmin settings
+      await page.waitForURL("/", { timeout: 10000 });
+      await page.goto("/settings/garmin");
+      await page.waitForLoadState("networkidle");
+    });
+
+    test("shows not connected initially for new user", async ({ page }) => {
+      // Verify initial state shows "Not Connected"
+      const notConnectedText = page.getByText(/not connected/i);
+      await expect(notConnectedText).toBeVisible();
+
+      // Token input should be visible
+      const tokenInput = page.locator("#tokenInput");
+      await expect(tokenInput).toBeVisible();
+
+      // Save button should be visible
+      const saveButton = page.getByRole("button", { name: /save tokens/i });
+      await expect(saveButton).toBeVisible();
+    });
+
+    test("can save valid tokens and become connected", async ({ page }) => {
+      // Verify initial state shows "Not Connected"
+      await expect(page.getByText(/not connected/i)).toBeVisible();
+
+      // Create valid token JSON - expires 90 days from now
+      const expiresAt = new Date();
+      expiresAt.setDate(expiresAt.getDate() + 90);
+
+      const validTokens = JSON.stringify({
+        oauth1: { token: "test-oauth1-token", secret: "test-oauth1-secret" },
+        oauth2: { access_token: "test-oauth2-access-token" },
+        expires_at: expiresAt.toISOString(),
+      });
+
+      // Enter tokens in textarea
+      const tokenInput = page.locator("#tokenInput");
+      await tokenInput.fill(validTokens);
+
+      // Click Save Tokens button
+      const saveButton = page.getByRole("button", { name: /save tokens/i });
+      await saveButton.click();
+
+      // Wait for success toast - sonner renders toasts with role="status"
+      const successToast = page.getByText(/tokens saved successfully/i);
+      await expect(successToast).toBeVisible({ timeout: 10000 });
+
+      // Verify status changes to "Connected" with green indicator
+      const connectedText = page.getByText("Connected", { exact: true });
+      await expect(connectedText).toBeVisible({ timeout: 10000 });
+
+      // Green indicator should be visible (the circular badge)
+      const greenIndicator = page.locator(".bg-green-500").first();
+      await expect(greenIndicator).toBeVisible();
+
+      // Disconnect button should now be visible
+      const disconnectButton = page.getByRole("button", {
+        name: /disconnect/i,
+      });
+      await expect(disconnectButton).toBeVisible();
+
+      // Token input should be hidden when connected
+      await expect(tokenInput).not.toBeVisible();
+    });
+
+    test("shows error toast for invalid JSON", async ({ page }) => {
+      const tokenInput = page.locator("#tokenInput");
+      await tokenInput.fill("not valid json");
+
+      const saveButton = page.getByRole("button", { name: /save tokens/i });
+      await saveButton.click();
+
+      // Error toast should appear
+      const errorToast = page.getByText(/invalid json/i);
+      await expect(errorToast).toBeVisible({ timeout: 5000 });
+    });
+
+    test("shows error toast for missing required fields", async ({ page }) => {
+      const tokenInput = page.locator("#tokenInput");
+      await tokenInput.fill('{"oauth1": {}}'); // Missing oauth2 and expires_at
+
+      const saveButton = page.getByRole("button", { name: /save tokens/i });
+      await saveButton.click();
+
+      // Error toast should appear for missing oauth2
+      const errorToast = page.getByText(/oauth2 is required/i);
+      await expect(errorToast).toBeVisible({ timeout: 5000 });
+    });
+
+    test("can disconnect after connecting", async ({ page }) => {
+      // First connect
+      const expiresAt = new Date();
+      expiresAt.setDate(expiresAt.getDate() + 90);
+
+      const validTokens = JSON.stringify({
+        oauth1: { token: "test-token", secret: "test-secret" },
+        oauth2: { access_token: "test-access-token" },
+        expires_at: expiresAt.toISOString(),
+      });
+
+      const tokenInput = page.locator("#tokenInput");
+      await tokenInput.fill(validTokens);
+      await page.getByRole("button", { name: /save tokens/i }).click();
+
+      // Wait for connected state
+      await expect(page.getByText("Connected", { exact: true })).toBeVisible({
+        timeout: 10000,
+      });
+
+      // Click disconnect
+      const disconnectButton = page.getByRole("button", {
+        name: /disconnect/i,
+      });
+      await disconnectButton.click();
+
+      // Wait for disconnect success toast
+      const successToast = page.getByText(/garmin disconnected/i);
+      await expect(successToast).toBeVisible({ timeout: 10000 });
+
+      // Verify status returns to "Not Connected"
+      await expect(page.getByText(/not connected/i)).toBeVisible({
+        timeout: 10000,
+      });
+
+      // Token input should be visible again
+      await expect(page.locator("#tokenInput")).toBeVisible();
+    });
+
+    test("shows days until expiry when connected", async ({ page }) => {
+      // Connect with tokens expiring in 45 days
+      const expiresAt = new Date();
+      expiresAt.setDate(expiresAt.getDate() + 45);
+
+      const validTokens = JSON.stringify({
+        oauth1: { token: "test-token", secret: "test-secret" },
+        oauth2: { access_token: "test-access-token" },
+        expires_at: expiresAt.toISOString(),
+      });
+
+      const tokenInput = page.locator("#tokenInput");
+      await tokenInput.fill(validTokens);
+      await page.getByRole("button", { name: /save tokens/i }).click();
+
+      // Wait for connected state
+      await expect(page.getByText("Connected", { exact: true })).toBeVisible({
+        timeout: 10000,
+      });
+
+      // Should show days until expiry (approximately 45 days)
+      const expiryText = page.getByText(/\d+ days/i);
+      await expect(expiryText).toBeVisible();
+    });
+  });
+});
diff --git a/playwright.config.ts b/playwright.config.ts
index 36babd1..5cbb6e1 100644
--- a/playwright.config.ts
+++ b/playwright.config.ts
@@ -54,6 +54,8 @@ export default defineConfig({
       // Use the test PocketBase instance (port 8091)
       NEXT_PUBLIC_POCKETBASE_URL: "http://127.0.0.1:8091",
       POCKETBASE_URL: "http://127.0.0.1:8091",
+      // Required for Garmin token encryption
+      ENCRYPTION_KEY: "e2e-test-encryption-key-32chars",
     },
   },
 });
diff --git a/scripts/setup-db.ts b/scripts/setup-db.ts
index 2f884b7..8761bb9 100644
--- a/scripts/setup-db.ts
+++ b/scripts/setup-db.ts
@@ -138,6 +138,57 @@ export const DAILY_LOGS_COLLECTION: CollectionDefinition = {
  */
 const REQUIRED_COLLECTIONS = [PERIOD_LOGS_COLLECTION, DAILY_LOGS_COLLECTION];
 
+/**
+ * Custom fields to add to the users collection.
+ * These are required for Garmin integration and app functionality.
+ */
+const USER_CUSTOM_FIELDS = [
+  { name: "garminConnected", type: "bool" },
+  { name: "garminOauth1Token", type: "text" },
+  { name: "garminOauth2Token", type: "text" },
+  { name: "garminTokenExpiresAt", type: "date" },
+  { name: "calendarToken", type: "text" },
+  { name: "lastPeriodDate", type: "date" },
+  { name: "cycleLength", type: "number" },
+  { name: "notificationTime", type: "text" },
+  { name: "timezone", type: "text" },
+  { name: "activeOverrides", type: "json" },
+];
+
+/**
+ * Adds custom fields to the users collection if they don't already exist.
+ * This is idempotent - safe to run multiple times.
+ */
+export async function addUserFields(pb: PocketBase): Promise<void> {
+  const usersCollection = await pb.collections.getOne("users");
+
+  // Get existing field names
+  const existingFieldNames = new Set(
+    (usersCollection.fields || []).map((f: { name: string }) => f.name),
+  );
+
+  // Filter to only new fields
+  const newFields = USER_CUSTOM_FIELDS.filter(
+    (f) => !existingFieldNames.has(f.name),
+  );
+
+  if (newFields.length > 0) {
+    // Combine existing fields with new ones
+    const allFields = [...(usersCollection.fields || []), ...newFields];
+
+    await pb.collections.update(usersCollection.id, {
+      fields: allFields,
+    });
+
+    console.log(
+      `  Added ${newFields.length} field(s) to users:`,
+      newFields.map((f) => f.name),
+    );
+  } else {
+    console.log("  All user fields already exist.");
+  }
+}
+
 /**
  * Gets the names of existing collections from PocketBase.
  */
@@ -242,6 +293,10 @@ async function main(): Promise<void> {
     process.exit(1);
   }
 
+  // Add custom fields to users collection
+  console.log("Checking users collection fields...");
+  await addUserFields(pb);
+
   // Get existing collections
   const existingNames = await getExistingCollectionNames(pb);
   console.log(
diff --git a/src/app/api/garmin/status/route.ts b/src/app/api/garmin/status/route.ts
index cfa27ea..5087ce4 100644
--- a/src/app/api/garmin/status/route.ts
+++ b/src/app/api/garmin/status/route.ts
@@ -8,7 +8,8 @@ import { daysUntilExpiry, isTokenExpired } from "@/lib/garmin";
 export const GET = withAuth(async (_request, user, pb) => {
   // Fetch fresh user data from database (auth store cookie may be stale)
   const freshUser = await pb.collection("users").getOne(user.id);
-  const connected = freshUser.garminConnected;
+  // Use strict equality to handle undefined (field missing from schema)
+  const connected = freshUser.garminConnected === true;
 
   if (!connected) {
     return NextResponse.json({
diff --git a/src/app/api/garmin/tokens/route.test.ts b/src/app/api/garmin/tokens/route.test.ts
index 3dabc7c..4a94058 100644
--- a/src/app/api/garmin/tokens/route.test.ts
+++ b/src/app/api/garmin/tokens/route.test.ts
@@ -12,10 +12,14 @@ let currentMockUser: User | null = null;
 // Track PocketBase update calls
 const mockPbUpdate = vi.fn().mockResolvedValue({});
 
+// Track PocketBase getOne calls - returns user with garminConnected: true after update
+const mockPbGetOne = vi.fn().mockResolvedValue({ garminConnected: true });
+
 // Create mock PocketBase client
 const mockPb = {
   collection: vi.fn(() => ({
     update: mockPbUpdate,
+    getOne: mockPbGetOne,
   })),
 };
 
diff --git a/src/app/api/garmin/tokens/route.ts b/src/app/api/garmin/tokens/route.ts
index a773915..59dfeba 100644
--- a/src/app/api/garmin/tokens/route.ts
+++ b/src/app/api/garmin/tokens/route.ts
@@ -5,6 +5,7 @@ import { NextResponse } from "next/server";
 import { withAuth } from "@/lib/auth-middleware";
 import { encrypt } from "@/lib/encryption";
 import { daysUntilExpiry } from "@/lib/garmin";
+import { logger } from "@/lib/logger";
 
 export const POST = withAuth(async (request, user, pb) => {
   const body = await request.json();
@@ -63,6 +64,26 @@ export const POST = withAuth(async (request, user, pb) => {
     garminConnected: true,
   });
 
+  // Verify the update persisted (catches schema issues where field doesn't exist)
+  const updatedUser = await pb.collection("users").getOne(user.id);
+  if (updatedUser.garminConnected !== true) {
+    logger.error(
+      {
+        userId: user.id,
+        expected: true,
+        actual: updatedUser.garminConnected,
+      },
+      "garminConnected field not persisted - check PocketBase schema",
+    );
+    return NextResponse.json(
+      {
+        error:
+          "Failed to save connection status. The garminConnected field may be missing from the database schema. Run pnpm db:setup to fix.",
+      },
+      { status: 500 },
+    );
+  }
+
   // Calculate days until expiry
   const expiryDays = daysUntilExpiry({
     oauth1: "",