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Mayhem wrote: ↑Sat Mar 08, 2025 11:45 am ... As soon as I deleted the oAuth connection to POP Peeper in Google....

What do you mean by the above comment? - please explain in detail what is is that you are doing as referenced above - that as you say then leads to you "... getting a 'Insert your security key into the USB port' security screen" that you mentioned.

I don't think you should have any such problems (as you've referenced) if you follow each of the steps as stated in this FAQ: https://www.esumsoft.com/pop-peeper/faq/?q=GmailAppPw (discussed in the previous page of this topic).

Mayhem -- thanks for the tip. Can you let me know about how many accounts you had converted before this problem?

I assume that you were needing to enable 2FA for these accounts (as opposed to just needing to create app-passwords)? While I understand that Google might be sensitive to lots of account changes from a single IP address, it also seems irrational when you're actually improving the security for these accounts.

To tag on to mjs' question -- does this mean that you had enabled 2FA, and then created an app password and it was after that you started getting the usb-key request? I'm not sure what to make of that... Is it possible you had created a passkey on a usb drive accidentally? did you have any usb drives installed at the time you enabled 2FA that aren't enabled now? What 2FA had you enabled?

Maybe try a different web browser.

mjs wrote: ↑Sat Mar 08, 2025 12:04 pm

Mayhem wrote: ↑Sat Mar 08, 2025 11:45 am ... As soon as I deleted the oAuth connection to POP Peeper in Google....

What do you mean by the above comment? - please explain in detail what is is that you are doing as referenced above - that as you say then leads to you "... getting a 'Insert your security key into the USB port' security screen" that you mentioned.

I went to myaccount.google.com, then to "Security" and then "Your connections to third-party apps & services" section and removed POP Peeper from the list via the "Delete all connection you have with POP Peeper" box.

Jeff wrote: ↑Sat Mar 08, 2025 12:48 pm Mayhem -- thanks for the tip. Can you let me know about how many accounts you had converted before this problem?

I assume that you were needing to enable 2FA for these accounts (as opposed to just needing to create app-passwords)? While I understand that Google might be sensitive to lots of account changes from a single IP address, it also seems irrational when you're actually improving the security for these accounts.

To tag on to mjs' question -- does this mean that you had enabled 2FA, and then created an app password and it was after that you started getting the usb-key request? I'm not sure what to make of that... Is it possible you had created a passkey on a usb drive accidentally? did you have any usb drives installed at the time you enabled 2FA that aren't enabled now? What 2FA had you enabled?

Maybe try a different web browser.

I was converting my second account when I got this issue. I've always had 2FA on all my Google accounts already - phone number and passkey (Windows Hello).

I've tried using a different browser (Firefox) and still have the issue. I'm contacting Google now to see what can be done about it. I'm still able to log in to the account and use Gmail, just not able to change any security settings.

Mayhem wrote: ↑Sat Mar 08, 2025 1:53 pm

mjs wrote: ↑Sat Mar 08, 2025 12:04 pm

Mayhem wrote: ↑Sat Mar 08, 2025 11:45 am ... As soon as I deleted the oAuth connection to POP Peeper in Google....

What do you mean by the above comment? - please explain in detail what is is that you are doing as referenced above - that as you say then leads to you "... getting a 'Insert your security key into the USB port' security screen" that you mentioned.

I went to myaccount.google.com, then to "Security" and then "Your connections to third-party apps & services" section and removed POP Peeper from the list via the "Delete all connection you have with POP Peeper" box.

Considering this is an extra step you've taken (i.e., directly above) that isn't included in the steps as stated in the FAQ https://www.esumsoft.com/pop-peeper/faq/?q=GmailAppPw link and taking into account your first Gmail account did not have any issues presumably as contrasted to the second Gmail account- I have a few questions:

1) So is it correct to say the first Gmail account did not have any issues with setting up an app-password and therefore has no problems and is successfully using an app-password in PP?
2) Did you do this same step you described above in the "Security" settings for that (first) Gmail account?
Or to rephrase - is it possible you did not do this same step in the first Gmail account you changed (i.e. when you successfully added the app-password)?
3) If it's possible you did not do the "Security" settings change for the first Gmail account (that did not have any problems) then if you have another (third) Gmail account; perhaps you could try setting the app-password for that third Gmail account and only do the steps as stated in this FAQ: https://www.esumsoft.com/pop-peeper/faq/?q=GmailAppPw (w/out including any extra steps of any kind).

To keep it simple (because your Gmail accounts are reportedly all already using "2-step verification", which btw, can be confirmed via the https://myaccount.google.com/apppasswords link discussed in the prior "2-step verification" steps) you would presumably only need to apply this last (app-password) step to your Gmail accounts: If the third Gmail account sets up the app-password successfully (this same method can be applied to any other Gmail accounts you may have) - we can then discuss the best approach to address the issues with second problematic Gmail account.

1) Yes, the first Gmail account had no issues, and is using an app-password to connect to POP Peeper.

2) Yes, I did the steps in the same order on the second account as I did on the first account.

3) It's not possible that I did not do the security changes on the first account. I am able to go to "Your connections to third-party apps & services" on that first account and see that "POP Peeper" is not listed.

I will attempt to do my third account tomorrow without my extra step (removing OAuth) and see what happens.

When I ran in to this issue, to me it felt like Google suspected something could be up and threw in a security measure to block it from happening. After all, I am removing a more secure OAuth setting and opting for a "less secure" app-password method. I'm very familiar with all the Google account options, so I'm wondering if the speed I was changing things was also was a factor.

The reason I'm even removing OAuth from the accounts is because I don't like to leave access methods to something I'm not even using.

I did a search for "insert your security key into the usb port" and it seems this is a somewhat common problem. Unfortunately, I didn't find any actual solutions. The most common solution seemed to be to go to:
Windows settings / Accounts / sign into apps with a physical security key / manage and then remove it.
Of course, the gotcha with this "solution" is that you'll need to insert your security key to access it...

Do you have access to another computer? If you have phone verification enabled on the google account (and presumably google isn't giving you that option because of the Windows security issue), then maybe trying to use a computer that doesn't have the passkey at all will give you a different verification option. Also: have you rebooted your computer?

That being said, I'm not sure that this is a Google or POP Peeper -based problem. Google obviously wants you to verify the account using your security method (Windows Hello) and it's Windows Security that is misbehaving.

OMG that's terrible news! I just wanted to add my main Workspace account to PopPeeper who I knew supported OAuth. Advanced Mail Check and Mail Check 2 never did, Pop Man has dropped OAuth as well - now it's definitly time to drop Google as email hoster and seach for another as there are no mail notifiers left. App Password is a nice thing for accounts which are rarely used to do the required regular login thing unless you lose them, but an actively used mail account needs to be able to be checked hasslefree from any webbrowser on any device.

Sorry for the update delay, I own a few websites and upgraded to a Xeon dedicated server, and it took more work than expected to get my websites back up and running. Anyways ..

I was able to solve the issue by using Google Chrome and logging in to my account. For some reason, that browser did not request I insert a USB key (Firefox and Edge did). I originally made the account changes on Edge, so I'm not sure if that plays any part in it.

I'm going to convert my other 3 accounts tomorrow, and if I run in to any issue I'll let you know.

It seems that once the App Password is set up, you can turn 2-Step Verification off.

Sorry, but it won't work. If POP Peeper is already connected to your gmail account when you disable 2FA, it will continue to work for a while because POP Peeper doesn't necessarily have to login every time it checks mail (feature of Imap/Idle). But once PP has to login again, the login will fail.

To be sure, I just tested this.

For anyone else that may be following this thread, please see this announcement regarding a new technique to use Oauth2 without the need to use 2FA.

Jeff wrote: ↑Wed Apr 23, 2025 7:01 pm Sorry, but it won't work. If POP Peeper is already connected to your gmail account when you disable 2FA, it will continue to work for a while because POP Peeper doesn't necessarily have to login every time it checks mail (feature of Imap/Idle). But once PP has to login again, the login will fail.

To be sure, I just tested this.

OK. Thanks for the verification.
I guess I'll switch my Gmail accounts to Oauth2 then as per your announcement.

It's the method I'll be using myself.

Jeff wrote: ↑Wed Apr 23, 2025 7:24 pm It's the method I'll be using myself.