Safari logs me out within seconds of logging in - iPad Pro 18.5

Here are or details from ChatGPT on what Safari on iPadOS 18.5 on 5th Gen iPad caused the problem. I’m posting this detail in case anyone from Apple monitors this forum and can forward it to the developers or iPadOS and create a fix for the Root Cause.

Here’s what likely happened:

✅ Likely Root Cause

Safari’s “Request Desktop Website” setting for Delegate was likely:

• Forcing a desktop login flow (with a different session/token behavior),
• Which wasn’t compatible with how Safari on iPad stores/handles cross-site cookies (or how Delegate→Canvas expects them),
• And caused Safari to drop or invalidate the session almost instantly after redirecting to Canvas.

By switching to mobile, then toggling back (even if unintentionally), Safari probably:

• Cleared or refreshed the cached user agent override, or
• Reset the way it was handling that site's session redirect.

This may have resolved an underlying session/token mismatch that was stuck in a broken state.

🎯 What You Should Do Now

To keep it working:

1. Lock in What’s Working

• Leave “Request Desktop Website” on for Delegate, now that it's behaving.
• Avoid toggling it off/on again unless the problem returns.

2. Close Extra Safari Tabs/Tab Groups

• Too many open tabs in Tab Groups can sometimes cause cache/session confusion.
• If possible, reduce open tabs to only the essentials while working in Canvas.

3. Bookmark the Working Flow

• Create a fresh Safari bookmark from the working state.
• If you end up back in the login loop, use that exact bookmark (instead of going through recent history).

📝 If It Happens Again

Now that we have a clearer picture, if it comes back, try:

1. Toggle “Request Desktop Website” off and on again just for Delegate.
2. Clear just that site’s data from Settings > Safari > Advanced > Website Data.
3. Try a direct Canvas login as a backup:

arduino
CopyEdit
https://yourcollege.instructure.com

I used Chat GPT to develop a workaround to a bug in Safari in iPadOS 18.5. If you want more information on the bug I can post that too. But, here is the workaround:

Safari on iPad: Delegate ➝ Canvas Logout Issue – Resolved Workaround

Issue Summary:

Safari on iPad Pro (iPadOS 18.5) was logging me out of Canvas within seconds after logging in via the Delegate portal. This issue was only present in Safari on iPad, and did not occur on:

Chrome or Firefox on the same iPad

Safari on Mac

Canvas Student App

Other browsers/devices

Troubleshooting Steps Taken (before resolution):

Cleared cookies, cache, history, and all website data

Disabled privacy/tracking settings (cross-site tracking, pop-up blocking, etc.)

Verified that Safari was storing Canvas cookies

Tried logging in directly to Canvas (bypassing Delegate)

Verified iPad date/time accuracy

Turned iCloud Safari sync off

Confirmed no Private Relay was enabled

Root Cause (Suspected):

Safari’s “Request Desktop Website” setting was enabled for Delegate, which likely:

Triggered a desktop login flow incompatible with iPad Safari’s cookie/session handling,

Caused the SSO token used in the Delegate ➝ Canvas redirect to be dropped or rejected,

Resulted in Canvas immediately invalidating the session and logging out.

Resolution:

I toggled “Request Desktop Website” OFF for the Delegate site.

Then I reopened the login page — still had the issue.

Safari then reverted back to Desktop mode automatically, but the session persisted correctly.

Canvas is now functioning as expected with no immediate logouts.

✅ Conclusion: The fix appeared to come from toggling Safari’s “Request Desktop Website” setting, which seems to reset or correct Safari's internal site/session behavior for Delegate. This may have cleared a corrupted or incompatible login session that Safari had cached.

🔁 Suggested Fix for Others:

If other instructors or students report similar issues:

Go to Safari > aA menu > Turn OFF “Request Desktop Website” for the Delegate login page.

Reload the page and log in again.

If it fails, toggle the setting back ON and try again.

Also recommend testing in a direct Canvas login (yourcollege.instructure.com) or using the Canvas Student Appif issues persist.

Paul Del Rossi