Problem with Two Factor Authentication with iCloud

[randyharris]

Recently iCloud started requiring Application Specific passwords for accounts with two factor authentication enabled.

I realized that I wasn't receiving my SABnzbd+ notifications, and it dawned on me that this App Specific password must be the issue.

I went to Manage My Apple ID and generated a password, in the CONFIG | NOTIFICATIONS | OPTIONAL Account Password, I enter this password, click Save, click Test and it works, I get the test email. Now close SAB web page, go back in, test, and it fails. Repeatable, happens every time.

No idea what the issue is, would sure appreciate help resolving.

[shypike]

Do you get any error message?

[randyharris]

I'm really not sure if it's something with SAB, or iCloud...

When I try again to send a test email I get a Red X graphic and the message "Failed to authenticate to mail server"

[psykix]

Did you manage to resolve this?

I can't get email to work with my iCloud account, and I have 2 factor authentication on also.

Created an App specific password and it worked the first time, but again like you experienced the next time you go back to the web page and test it fails.

[shypike]

I've tried, the results are very intermittent.
Sometimes it just works, at other times it doesn't.

[randyharris]

I always get the error in the setup page as described above (not the very first time), however, I HAVE been receiving my SAB notifications via email.

[psykix]

I always get the error in the setup page as described above (not the very first time), however, I HAVE been receiving my SAB notifications via email.

Ah.. well if that's the case then it's fine by me :-)

I haven't had anything download since setting it up so if it works regardless of the test failing then that's cool :-)

[psykix]

I've tried, the results are very intermittent.
Sometimes it just works, at other times it doesn't.

Dontcha just hate those type of problems!!

[shypike]

Dontcha just hate those type of problems!!

Yes, that's the worst kind.
At least it's not in the core functionality.
I'll be looking at an alternative email method in a later release.

[jcfp]

Can't find it now, but wasn't there a thread recently about similar weirdness with gmail? iirc people were getting denied access when securely connecting to the gmail server using the correct credentials, based on some security related settings of their account? May be hard to fix on the sab end of things.

[shypike]

Wasn't that about application-specific passwords for two-factor users?

[psykix]

I can confirm that setting up iCloud using two factor authentication and with app specific password and testing the first time is successful. Subsequent tests fail to authenticate, but the email notifications do in fact work, so not a big issue really :-)

[shypike]

Thanks, I will use the debugger to find out what's going on.

[shypike]

I did find a problem.
When testing the email servers with existing (already stored) parameters, things fail.
The reason is that the password has been substituted with asterisks (for security reasons).
Of course in that case, the password should be read from the INI file instead.
The problem isn't specific for iCloud but for any email server that requires a password.

I haven't seen issues with normal email notifications when using iCloud with app-specific passwords.
I have improved the logging a bit so that the next release will at least provide more info when things go wrong.