Page 1 of 1

Outlook OAUTH issues

Posted: Fri Jun 06, 2025 10:11 am
by willi.am
I think I am the problem, and below is not a bug, but I can't figure out how to solve it.

So I am posting it here, maybe someone else has the same issues.

Code: Select all

--- Version ---
OS: Windows 11 (x64) 
POP Peeper: 5.6.3.0
Webmail: 5.1.0.0 (disabled)
SSL: 3.0.16.1
IMAP: 5.6.3.0
SendMail: 5.6.3.0
Profile Picture: 5.6.3.0 (disabled)
AntiJunk: 5.6.3.0 (disabled)
Spell Checker: 5.6.3.0
Trusted Sites: 5.6.3.0 (disabled)
PPTweaker: 5.6.3.0
Updater: 1.0.0.0

Program folder: F:\***
Ini file: F:\***
Data folder: F:\***

--- Error ---
Outlook - *** [1000: IMAP] ['outlook.office365.com' (993) SSL: 1] [Smtp: 'smtp.office365.com' (587) SSL: 2] [oauth: 1] [consec: 5] [enabled: 1]
- Oauth2 error -- There was a problem connecting to the Oauth2 server. Try again later or reset Oauth2 if the problem persists.  Reset Oauth2: pp://OAuth2?***= Edit account: pp://EditAccount?***=

Outlook - *** [1000: IMAP] ['outlook.office365.com' (993) SSL: 1] [Smtp: 'smtp.office365.com' (587) SSL: 2] [oauth: 1] [consec: 5] [enabled: 1]
- Oauth2 error -- There was a problem connecting to the Oauth2 server. Try again later or reset Oauth2 if the problem persists.  Reset Oauth2: pp://OAuth2?***= Edit account: pp://EditAccount?***=

Outlook - *** [1000: IMAP] ['outlook.office365.com' (993) SSL: 1] [Smtp: 'smtp.office365.com' (587) SSL: 2] [oauth: 1] [consec: 5] [enabled: 1]
- Oauth2 error -- There was a problem connecting to the Oauth2 server. Try again later or reset Oauth2 if the problem persists.  Reset Oauth2: pp://OAuth2?***= Edit account: pp://EditAccount?***=

This is my error-log from Pop Peeper Pro (licensed).

I have some Outlook accounts and all work well, until "suddenly" the authorization stops working (and the above error messages pop up).

Sometimes 1 out of 3 accounts does this, sometimes all and when the work... they just work. In between I do not do anything else with settings or something.

When I wait (sometimes for hours) the error disappear and when I turn of the internet (disabling my router) or switching to another network (from LAN to WiFi) the problem CAN be solved... untit it starts hunting me.

The weird thing is, when I "reset" the oAuth Pop Peeper freezes like this;

1. Click on "reset" oAuth
2. Window is shown with the 3 options (web/ form/ inline code)
3. Browser opens (with Outlook oAuth page)
4. All is authorized, browser returns to Pop Peeper (with screen 2.)
5. Pop Peeper freezes; nothing works, wait for a minute or two
6. Pop Peeper comes alive, telling me "oAuth failed" (which did)

Like I said, when I wait for a while, sometimes hours, leaving my computer "on" and continue with my work, it all starts working again like magic.

Weird, he!

Image
Image
Image

BTW. There was a problem connecting to the Oauth2 server can be true (maybe something is blocking it at random intervals?) but when I hit 'authorize' I can connect to the server without problems (in the browser).

O, and none of the three options does work: they all freeze with the same error-message after some time.

Re: Outlook OAUTH issues

Posted: Fri Jun 06, 2025 3:05 pm
by Jeff
BTW. There was a problem connecting to the Oauth2 server can be true (maybe something is blocking it at random intervals?) but when I hit 'authorize' I can connect to the server without problems (in the browser).
The URL used for the user-facing login and the URL used for the back-end authentication are 2 different servers, so it's entirely possible for one URL to work and not the other.
4. All is authorized, browser returns to Pop Peeper (with screen 2.)
5. Pop Peeper freezes; nothing works, wait for a minute or two
Your browser will send a "code" back to POP Peeper and it's at this point that PP will validate this code with the Oauth2 server. This is actually the first time that PP will need to communicate with the Oauth2 server (as far as this process is concerned), so it kind of makes sense that it fails at this point, too.



Here are some suggestions:
- Reboot your computer
- Restart your network router
- Make sure Windows doesn't have any pending updates

If that doesn't fix it:
- How often does this occur?
- Do you have any other account types (ie. gmail, yahoo) that use Oauth2? (just wondering if it's specific to outlook or if you just don't have other accounts to prove/disprove that speculation)
- Does exiting/restarting PP fix it?
- Are you using any 3rd party "security" programs that may affect/monitor https traffic?

Also, unless you strongly suspect that you really do need to re-oauth the Outlook accounts, I would recommend against resetting Oauth2. That can sometimes exacerbate problems because it may look suspicious to Outlook.

Re: Outlook OAUTH issues

Posted: Fri Jun 06, 2025 4:19 pm
by willi.am
- Restart computer : did it several times, didn't help
- Restart POP Peeper : idem
- Updates 4 Windows : nope
- How often : several times a day
- Other accounts : POP3 / IMAP4 (own domainserver) and Outlook, so NO Gmail
- 3rd party soft : nope, only Windows Defender (build in scanner)

The problems starts with Pop Peeper saying in the statusbar "xxx@outlook.com : Logging In...", which takes ages.

Then account show underlined (error) and the yellow /!\ is shown in the statusbar.

I have the exact same set-up on another computer (Windows tablet) and there it's working fine... so I guess something at my desktop doesn't like me :-)

Well, I think it's not a PP bug, so you can close it... unless another forummember has the Golden Idea!

Re: Outlook OAUTH issues

Posted: Mon Jun 09, 2025 4:29 pm
by Jeff
It seems like a connection problem to me, but I'm not sure why it would be specific to the Outlook oauth2 server, especially if you have another device that it works with (and is presumably on the same internet connection).

One thing that may or may not help is to try to ping the microsoft server and see if that reflects the same problem:
ping login.microsoftonline.com -t

The '-t' will keep pinging until you stop it (Ctrl+C); I'd suggest letting it run for 5-10 minutes and then get final statistics. Any packet loss > 0% could be a sign of issues.