#1817 ✓resolved
Richard Chick

Unable to connect to iCloud using two-factor authentication

Reported by Richard Chick | August 22nd, 2017 @ 11:28 AM

I have not been able to connect MailMate to my iCloud accounts. I have obtained the app-specific passwords and inserted them in the IMAP AND SMTP password fields but the [Enter password for “xxxxx@mac.com” at “p60-imap.mail.me.com”] popup keeps reappearing. How can I resolve this?

Comments and changes to this ticket

  • benny

    benny August 22nd, 2017 @ 07:11 PM

    First, just use imap.mail.me.com and smtp.mail.me.com since these are the ones recommended by Apple. Second, make sure you use username only for IMAP and username@domain.com for SMTP. This is weird, but it's what Apple recommends.

    Also, try the latest test release of MailMate like this: Hold down ⌥ when clicking “Check Now” in the Software Update preferences pane.

    Let me know if it still fails.

  • Richard

    Richard August 23rd, 2017 @ 11:39 AM

    I tried changing my account settings as you suggested, first without updating MailMate, and my primary address (rchick@xxx.com) was then working but the account seemed to continue syncing indefinitely. My secondary address (dickchk@xxxxx.com) still failed to connect with a password error.
    I then updated per your instructions to Version 1.9.7 (5409) and upon restarting my primary address connected and synced properly. My secondary address still failed to connect. I tried a new app-specific password but still no luck. I also tried adding the "@icloud.com" for the imap user name without success. I'm wondering if there is a problem with the smtp user name when the two apple addresses are obtained in different eras. Apple Mail accepts dickchk@xxxxx.com for the smtp server but I wonder if they're performing a translation not available to 3rd party.

    I should have specified my equipment: I'm using a recently purchased 2013 Mac Pro running the latest version of Sierra.

  • benny

    benny August 23rd, 2017 @ 01:18 PM

    I'm glad some of it works.

    So, if I understand correctly then only dickchk fails now and only for IMAP. You can try connecting manually in a Terminal window like this:

    openssl s_client -connect imap.mail.me.com:993

    When it's connected then authenticate like this:

    0 LOGIN dickchk xxxx-xxxx-xxxx-xxxx

    The latter should be your app specific password. If it succeeds then logout like this:

    0 LOGOUT

    Note: Don't list your email addresses in the tickets, because they might be scraped by spammers. I've anonymized them for you.

  • Richard

    Richard August 23rd, 2017 @ 03:40 PM

    The openssl terminal command failed with the following response.
    unknown option imap.mail.me.com:993

    I also realized that I had not tried sending from the rchick account. When I tried to send an email to one of my other fully working accounts I got a failure report through from the mac postmaster saying "Remote SMTP server has rejected address". The address being rejected is in use and working with MailMate.

    So my status is that only my primary Apple email address is working to receive email but not to send email. My secondary Apple address is unable to send, receive or go online.

  • benny

    benny August 23rd, 2017 @ 03:58 PM

    I assume you have other means to send emails. Could you send me these files:

    ~/Library/Application Support/MailMate/Sources.plist
    ~/Library/Application Support/MailMate/Submission.plist

    MailMate doesn't control what a given SMTP server is going to reject or not, but maybe I can see a configuration issue in these files.

    The error you got from the Terminal window doesn't make sense to me. Sounds like you might have skipped the -connect argument. Try copy/paste if you didn't do this the first time.

    Thanks in advance.

  • benny

    benny August 23rd, 2017 @ 04:00 PM

    I forgot to note that there's a direct email address to me on this page.

  • Richard

    Richard August 24th, 2017 @ 01:05 PM

    I tried using MailMate and sending a reply to the direct email address but received,

     "We received an email from this address that had problems being processed
      into a new Lighthouse ticket:
      You do not have access to post to the MailMate project.
      FILE BUG
      support@lighthouseapp.com or http://help.lighthouseapp.com"

    I'm sure this is operator error on my part but I need to just stick to this online post until I get things under control.

    After turning my attention to my other accounts I find that, in addition to my issues with iCloud, I have problems with Yahoo, and Gmail. I noted the special instructions regarding Gmail in the help system but does not seem to apply to my issue.

    My status is as follows.

    iCloud (as previously reported):
        primary account, IMAP (apparently working), SMTP (not sending)
        secondary account, password rejected, cannot bring online
        initially IMAP seemed to be working. inbox contains mail up to Aug 21. Now however the account         is labeled “(offline)”. I logged into Google online and it reports “A less secure app was blocked from signing in” at about the time I attempted to bring it online. I am not using 2-level authentication
        account rejected, cannot bring online, I have checked password by logging into Yahoo online and reviewing Yahoo account setup instructions for user name, etc.  I am not using 2-level authentication
  • benny

    benny August 24th, 2017 @ 01:44 PM

    Note that I also replied by email.

    It's an awful lot of issues you have, but we'll take them one by one:

    Lighthouse: I think this happens if you end up sending from a different email address than the one you registered with.

    iCloud: Did you try what I wrote in the email? Using a Terminal window ensures that a MailMate bug cannot be involved.

    Gmail: Right-click the account under SOURCES and select “Take Online”. What happens? Also, make sure that you have OAuth2 authentication enabled in the account settings.

    Yahoo: I have checked my test account for Yahoo and it still works. Therefore it's unlikely to be a general issue. I think we'll leave this one until the other accounts work.

  • Richard

    Richard August 24th, 2017 @ 09:11 PM

    Regarding iCloud
    I issued the terminal commands as you instructed and supplied the app-specific password stored in my keychain from a previous test. The process failed with the statement, "0 NO [AUTHENTICATIONFAILED] Authentication failed closed" I then applied for a new app-specific password and issued the commands again with the same results This may prove that the problem is not a MailMate problem but it is still a problem for me. It seems like the Apple app-specific password is just not working.

    Regarding Google
    The problem has been resolved. I found it necessary to turn off OAuth2 in order to enter the Gmail passwords for both IMAP and SMTP servers and assumed that it should remain off or it would override the correct passwords. This is not very intuitive for the user.

  • Richard

    Richard August 25th, 2017 @ 01:28 PM

    Regarding Yahoo
    I was not using a 2nd level password. That issue is now resolved.

    Regarding iCloud
    My primary Apple address is now working for both send and receive. -not sure why this didn't work before, possible operator error.

    All my email issues are now resolved EXCEPT Apple secondary (and only) iCloud address which I have yet to bring online with app-specific password.

  • benny

    benny August 25th, 2017 @ 01:36 PM

    Thanks for the update.

    Gmail: Perhaps it would be better if MailMate hides the password field when OAuth2 is enabled (instead of just disabling it).

    Yahoo: I don't know what a 2nd level password is, but I'm glad it works.

    iCloud: Could you try again and then use copy/paste to send me the output via email? Remember to change the password (e.g., replace with x'es) to make sure I don't gain access to your account. I'll see if I can spot anything suspicious.

    (Also, make sure that you generate the app-specific password for the same iCloud account you are trying to get access to.)

  • benny

    benny August 25th, 2017 @ 01:42 PM

    Gmail: I've done this for the next update of MailMate (hiding the password fields).

  • benny

    benny September 12th, 2017 @ 07:01 PM

    • State changed from “new” to “resolved”

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