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Monitor your login flow (and know before customers do)

Login is the front door. If it sticks, everything else stops.
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Why login breaks

Login issues are common and usually silent. Here are the most frequent culprits:

Redirect loops after config changes

Cookies or session issues across environments

SSO provider hiccups (SAML timeouts, token expiry)

UI changes that hide or rename the login button

What to monitor (starter checklist)

Login page loads successfully

Enter credentials and submit

Assert: dashboard loads OR "Welcome back" text appears

Assert: no error banner appears

Optional: logout completes cleanly

Common failure modes

These are the issues that won't show up in uptime monitoring:

"Spinner forever" after clicking submit

401/403 after successful authentication

CAPTCHA or MFA blocking automation (handle with a dedicated test user and bypass policy)

Quick setup outline

1

Create a dedicated test user

2

Record or define the login steps

3

Add 2–3 success assertions

4

Schedule runs and set alert routing

Alert routing

Route login failures to the right people: Slack for the on-call channel, email for founders or a daily digest.

Frequently asked questions

Yes. Use a dedicated test user that authenticates through your SSO provider. For SAML-based SSO, the synthetic check flows through the same redirect dance a real user would.

For test accounts, set up a bypass policy or use TOTP with a known seed so the automation can generate valid codes. Never disable MFA for real users.

Start with one. If you serve users globally and login depends on region-specific infrastructure (CDN, SSO endpoints), add a second region later.

For TOTP-based MFA, use a dedicated synthetic test user whose second factor is stored in a secure secrets vault and generate time-based codes at runtime (never hardcode codes). For SMS/push MFA, prefer an alternate factor for the synthetic user (TOTP or backup codes) because SMS inbox and push approval aren’t reliably automatable. If your IdP supports it, create a “monitoring” policy that requires MFA but allows a stable factor (TOTP) and restrict the user by IP/device, least-privilege roles, and strict rate limits. Always separate synthetic users from real users and rotate secrets regularly.

Treat SSO as a multi-hop journey: app → IdP → app callback. Your checks should assert each redirect target (host + path), validate the final landing page, and capture cookies set on each domain. Common breakpoints include changed callback URLs, missing allowed redirect URIs, SameSite cookie changes, and IdP policy updates. Run at least one check against the full SSO flow and another against your “local login” (if you have it) so you can distinguish IdP outages from app regressions.

Add explicit assertions on redirect count and final URL. A redirect loop often manifests as repeated 302s between /login and /app (or /auth/callback). Best practice: fail the check if redirects exceed a threshold (e.g., >10) or if the journey revisits the same URL pattern multiple times. Also assert that a post-login session cookie is present and that a known authenticated element appears (e.g., user avatar, account menu). Screenshots at each step make it obvious whether the user is stuck at an IdP consent screen, a CSRF error page, or a blank callback route.

Validate the presence and attributes of the cookies that represent authentication/session state: domain scope (apex vs subdomain), Secure flag (required on HTTPS), HttpOnly, SameSite (Lax/None), and TTL/expiry behavior. Many real-world failures come from cross-site redirects in SSO combined with SameSite=Lax or missing SameSite=None;Secure on third-party contexts. Also watch for environment mismatches (cookie domain set to staging.example.com while running on app.example.com) and clock skew causing immediate expiry.

Use a dedicated monitoring account, keep run frequency reasonable (e.g., every 5–15 minutes per region), and configure stable IP ranges if your WAF supports allowlisting. Add realistic pacing between steps and retry logic only on network/transient failures (don’t brute-force). Ensure lockout policies exclude the synthetic user or set a higher threshold, and alert on repeated failures to prevent the check from repeatedly failing and escalating to a lockout. If you use Cloudflare/Datadog/WAF challenges, configure a bypass rule for the synthetic user’s path or tokenized header.

At minimum: (1) correct page title/heading for login, (2) successful form submission response/redirect, (3) session established (cookie/local storage token present), (4) authenticated UI element visible, (5) critical API call returns 200 (e.g., /me or /session), and (6) no console errors for key routes (optional but useful). Also assert performance thresholds (e.g., login completes <5s) so you catch slowdowns before they become timeouts.

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By the numbers

The average cost of downtime is about $5,600 per minute (often cited as ~$300K per hour).

Gartner (widely cited estimate) (2014)

A 1-second delay in page response can reduce conversions by ~7%.

Akamai (performance research frequently cited in web performance discussions) (2017)

Organizations with higher observability maturity report faster incident detection and resolution than less mature peers.

Splunk, The State of Observability (2023)

MTTR and alert fatigue remain top operational challenges; teams continue investing in synthetic and end-user monitoring to catch customer-impacting issues earlier.

Datadog, State of Monitoring / Observability reporting (2024)

Real-world examples

Redirect URI regression after IdP configuration change

Scenario: A small SaaS uses Okta SSO. An admin updates the Okta app and accidentally removes one callback URL. Users hit /auth/callback and get bounced back to /login with no clear error.

Outcome: A scheduled synthetic login journey fails within 5 minutes, showing repeated 302 redirects between /login and /auth/callback. The alert includes the failing step + screenshot, cutting time-to-detect from “next customer ticket” to minutes and preventing a morning of blocked logins.

SameSite cookie change breaks cross-site SSO on Chrome

Scenario: An auth library upgrade changes the session cookie from SameSite=None;Secure to SameSite=Lax. Local login still works, but SSO flows that rely on cross-site redirects silently drop the cookie on return.

Outcome: The check validates cookie attributes and fails immediately after the IdP redirect, with a screenshot showing the user returned to /login. The team rolls back the change and adds a cookie-attribute assertion to prevent recurrence.

Bot protection challenge blocks real users (and your monitoring catches it)

Scenario: A WAF rule is tightened and starts challenging /login POST requests. Real customers see intermittent CAPTCHA/challenges that the frontend doesn’t handle well.

Outcome: Synthetic runs from two regions show a sudden spike in step failures at form submit, with screenshots of the challenge page. The team adds an allowlist rule for the synthetic user and adjusts WAF sensitivity for authenticated flows, reducing failed logins and support tickets.

Login works, but post-login API is broken (false sense of ‘up’)

Scenario: After login, the app loads /me to render the dashboard. A backend deploy breaks /me with 500s, so users land on a blank dashboard even though authentication succeeded.

Outcome: The journey includes an assertion that /me returns 200 and the dashboard renders a known element. The monitor fails on the authenticated step, catching a production regression that basic uptime checks would miss.

Key insights

1.

Login failures are often “partial outages”: the site is up, but authentication/session establishment is broken—synthetic user journeys catch what ping checks and basic HTTP 200 monitors miss.

2.

Redirect loops and login bounces are usually configuration drift (allowed redirect URIs, cookie domain/SameSite, proxy headers like X-Forwarded-Proto) and are detectable with redirect-count + final-URL assertions.

3.

SSO adds multiple failure domains (your app, IdP, DNS, certificate chain, third-party scripts). Monitoring both SSO and non-SSO paths helps you quickly isolate whether the issue is internal or upstream.

4.

Cookie/session issues are a top real-world cause of “it works locally but not in prod” because of HTTPS-only flags, cross-site redirects, and environment-specific domains—assert cookie presence and attributes, not just page content.

5.

MFA is monitorable without compromising security by using dedicated synthetic users, vault-backed secrets, least-privilege roles, and stable factors like TOTP instead of SMS/push.

6.

The most actionable alerts include step-level failure context: last successful step, failing selector/assertion, final URL, and screenshots—this reduces time-to-triage for small teams without a 24/7 NOC.

7.

Run login checks from multiple regions and at realistic cadence (5–15 minutes) to distinguish global auth outages from regional CDN/DNS/IdP routing issues and to avoid rate limits/lockouts.

Pro tips

💡

Add a “/me” (or “/session”) assertion after login: verify it returns 200 and includes the synthetic user’s ID/email. This catches post-login breakages that look like successful auth but result in a broken app.

💡

Create two monitors: (1) local email/password login, (2) SSO login. When one fails and the other passes, you instantly know whether to look at IdP config/policies vs your own auth code.

💡

Instrument redirect-loop detection: fail if redirects >10 or if the same URL repeats. Pair it with a cookie assertion (session cookie present + correct SameSite/Secure) to pinpoint whether the loop is caused by missing session state.

How CheckyWorky compares

vs Datadog Synthetics

Powerful enterprise platform with deep integrations, but can be heavier to configure and costlier at scale. CheckyWorky emphasizes small-team-friendly setup for core SaaS login journeys with clear step failure context (screenshots + failing step) and pragmatic defaults.

vs Checkly

Developer-centric synthetic monitoring with code-first Playwright checks. CheckyWorky focuses on “pretend customer” flows with opinionated UX for common SaaS login failure modes (redirect loops, cookie/session assertions, post-login API checks) and faster time-to-value for teams that don’t want to maintain lots of test code.

vs UptimeRobot

Great for basic uptime (ping/HTTP keyword) but not designed for multi-step authenticated journeys. CheckyWorky runs real login flows end-to-end and verifies session establishment and post-login behavior, which is where many customer-impacting failures happen.

Pick one journey and set it up in under 10 minutes.

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