issue with password changing

I'm not sure what triggers this behavior, but it sounds like something I
should be able to reproduce. My best guess is that MailMate fails to
properly update the passwords saved in the system keychain.

Try the following: Launch the “Keychain Access” application and
delete any passwords related to the Gmail account. Then launch MailMate
and try to make it save the password in the keychain again. I would
expect this to work since it's equivalent to starting all over with
MailMate.

You are also welcome to analyze the existing items in the keychain in
order to help me reproduce the issue.

Hi Benny,

Thanks very much for your help.

I have tried what you recommend, but it does not fix the issue.

Also, I have this message when I want to send an email :

Unexpected return code 535 (expected 235):
“5.7.8 Username and Password not accepted. Learn more at 5.7.8 https://support.google.com/mail/answer/14257 ew10sm7992583wic.22 - gsmtp”.
Please enter password for user name

Have you tried following that link and attempt some of the solutions? I don't care much for Google's “less secure” label on that page. It's a problem for Google that a password provides access to much more than IMAP, but it doesn't make the connection between an email client and the Google IMAP server “less secure”.

Alternatively, MailMate has experimental support for the XOAUTH2 protocol which seems to be what Google would like to replace the classic login methods. Read more about that here. Other users have reported that this works well, but this browser-based login method is currently not very user friendly.

Yes Benny, I tried all the solutions in that link and the problem is still here.

As I am still on the 30 days trial with MailMate, I won't purchase it and I will go back to Apple MAIL. It is really a pity as I have found MailMate quite efficient except this issue.

Thanks anyway for your help

Very understandable, but could I convince you to try the XOAUTH2 solution in the link I provided. I'd like to know it that fails as well.

To be honest, when I first open your link about XOAUTH2 protocol, it looked so "high level IT" for me that I gave up right away...

I am happy to try, but I am not sure to understand what to do.

Do you want me to enter "defaults write com.freron.MailMate MmXOAUTH2Enabled -bool YES" in the MailMate browser window that appears when I open MailMate ? I mean the one asking for my password ?

Sorry, the hidden preferences are configured using a Terminal window (Applications/Utilities). You simply paste that line into a Terminal window and then relaunch MailMate:

defaults write com.freron.MailMate MmXOAUTH2Enabled -bool YES

When MailMate tries to connect to the server then the browser window is automatically shown when the password requester is opened. You then copy/paste the provided code to the password requester in MailMate. That should be it.

I hope that helps.

Sorry, but what do you mean by "paste that line into a Terminal window" ?

Are you talking about the windows that appears when I launch MailMate ? I mean the one with the following message : Server response: “D1 NO [AUTHENTICATIONFAILED] Invalid credentials (Failure)”. Command attempted: “D1 AUTHENTICATE PLAIN ••••••••••”. Please enter password for user name “xxxes3” ?

I should have been more explicit. “Terminal” is an application residing in “Applications/Utilities/”. If you launch that then you'll see a window which can be used to enter various text commands. I want you to enter (copy/paste) the line into that window (and hit return). This executes a command named “defaults” which can write to the preferences used by MailMate.

Remember to relaunch MailMate after doing this.

I did what you recommend, but it is getting worse in a way. Now, every time I launch MailMate (and first time I want to send an email after a relaunching), a Google window opens in my Chrome browser asking me to paste a very long code (supplied by Google) to a windows that opens in MailMate...

And what happens when you do paste the code in the MailMate password window? Does it work initially? Or does the password requester immediately reappear?

Note that it'll happen once for every Gmail account you have (in case you have multiple accounts). This could quickly become confusing.

The password requester does not reappear, but instead I have this Google procedure all the time. For instance as soon as I want to send an email...
Is there any way to come back to the previous (before what I did about the XOAUTH2 protocol), please ?

Actually, I have only one Gmail account on MailMate.

That is very strange. I'm starting to suspect that there is a problem with your system keychain in general. You disable XOAUTH2 like this:

defaults write com.freron.MailMate MmXOAUTH2Enabled -bool NO