Users are experiencing POP3 authentication failures with Gmail in Discourse due to Google’s deprecation of “less secure app access” as of May 30, 2022. Amicable reports the issue after five years of stable operation and references an older workaround involving application passwords. agungor advises enabling 2FA and generating an App Password for Discourse, noting Google’s policy change. Amicable confirms success but warns of Google’s security alerts and auto-rejection of initial attempts, recommending users monitor their Gmail inbox to approve changes. Richie follows the steps — enabling 2FA, creating an App Password, updating Discourse’s pop3 polling password, and confirming security prompts — but initially sees an error: Application-specific password required. After waiting, Richie reports the issue resolved. DavidO observes a connection but still encounters 535-5.7.8 Username and Password not accepted when checking Gmail Sent items, suggesting the fix may require additional time or configuration. The consensus is that using App Passwords with 2FA is now required, and users should allow time for Google’s systems to propagate changes and monitor security alerts.
It looks like Google has changed POP3 access and this has led to my instance failing to poll messages after running smoothly for 5 years.
I found an older fix for this here: Gmail POP3 authentication failed — switch to application password . I followed the gmail link provided in order to switch the service to application password only but it seems Google adjusted their policy on May 30 2022.
Can anyone kindly advise how Gmail Pop3 should now be setup in Discourse?
I recommend turning on 2FA on the account and setting up an App Password for Discourse. The policy change is about the “allow less secure app access” option being deprecated. More info on this here:
Thank you, That’s now working 
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A warning for anyone else going through this - Google will likely fire off security alerts. The algos went as far as auto-dumping my first attempt 
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Check the inbox of the gmail account you’ve setup as you go through this process so you can confirm to their algos that is you performing the changes.
Thanks @JammyDodger for pointing me towards this topic.
I have the same problem that @Amicable reported here.
Can I just check the process?
I enabled 2FA on my gmail account. This then revealed/added the option for me to create App Passwords at https://myaccount.google.com/security
I then created a new app, and copied the 16 digit password.
I checked my inbox and saw the security emails you mentioned, I followed them through and confirmed “it was me”.
Then I went to my Discourse settings and changed the pop3 polling password setting, removing the old password and replacing it with the 16 digit app-password.
Is there anything else I need to do? I’m now seeing this is my logs:
Job exception: -ERR [AUTH] Application-specific password required: https://support.google.com/accounts/answer/185833
Have I missed something? 
Do I need to restart anything?
I waited some time, this seems to have rectified itself.
Thanks for the info here everyone 
