Q: Can't connect so smtp-Server since Mavericks update.

Hi Pascal,

I am facing the same issue. I tried disabling the SSL on the outgoing mail server and it works intermittently.

Even I am searching a solution!!

Cheers!!

Rahul.

I have the same problem. Both POP and SMTP stopped working after the upgrade to OS X 10.9 - I changed the POP server name from digits to words and it is working but SMTP continus to not work. Any help will be vastly appreciated!

Thanks - Tapan.

I began having this same problem only with my work SMTP server right after upgrading to Mavericks both in an iMac and in a MacBook Pro. Emails were not going out and I was either receiving time out messages for the connection with the server or getting a window stating that the server appeared offline.  

In my case it seems that the problem has been solved by accepting the security certificate of the SMTP server. For that I had to untick the SSL option on the SMTP advanced tab; then close down Mail, open Mail again and then going to the SMTP advanced tab and tick again the SSL option. Then a message asking for me to accept the certificate appeared. I ticked the acceptance, put my password and right away listened sweet sound of a ten email stack flying away from ougoing email tray.

Hope this helps.

Regards,

Hi,

What I did, just disable SSL protocol and it worked for me, but what strange, mine server provider says that it should be on.

regards

Hey, that worked for me too!! It had stopped out of the blue but that trick seems to have done it - thanks!!

OK, I was having the same problem and disabling SSL didn't work for me. Other solutions suggested in other forum threads also didn't work, but I've finally found a solution that works for me. Here it is in the hopes it will help other people:

In summary, I realized that the root of the problem was, as mentioned in the original post above, that the SSL certificate wasn't being accepted (-9807 Invalid certificate chain). This was because the SMTP server's certificate was expired. I did not want to try to convince my provider to fix it - instead I wanted to fix it myself on my end.

The solution was to import the SSL certificate to my keychain and flag it to "Always trust". However, getting the certificate was a bit tricky, as Mac Mail was not giving me the option. Here's how I did it:

1. I downloaded and installed Thunderbird (Mozilla's mail client, Firefox's cousin) and configured my problem email address there.

2. I tried sending an email from Thunderbird and then I got a pop-up saying that the certificate was not valid. On that pop-up, there is an option to view the certificate and then export it. So, I chose to export it to a .pem file (used option "with chain") to my desktop.

3. I dragged the .pem file and dropped it on my keychain icon on the dock (double clicking on it should work too). Then Keychain Access popped up (it imports the certificate automatically) so then I flagged the certificate as "Always Trust" and saved it.

After doing this, I was able to send SMTP email from Mac Mail.

At this point, you can remove Thunderbird, but first see the note below.

Note: Is this only works intermittently for you, it may be that you are being served by more than one SMTP server, so in that case  you would need to do this for every one of them (import every certificate and flag as "Always Trust".

Hope this helps others.

Wow Pismo-C, thanks!  After scouring all of the discussion boards and finding the myriad and varied solutions users have found to this issue your solution is the first and only one to have worked for me.  Ingenious idea and something I would have never thought of.

Just to summarize for others what my situation was, after upgrading to Mavericks the SMTP server on one of my wife's email accounts (a GoDaddy account associated with her business domain) stopped working.  The gmail SMTP continued to work just fine.  Her settings previously were SMTP Port 465 and SSL ON.  I would get the error message that the server timed-out.  Like other users, at random times and after resetting several things I could get this to send a few times but then it would invariably stop working again after a period of time for no known reason.  It seemed the server was initially allowing traffic through but then blocking.  I tried every port, SSL on and off with each one, and adding different types of authentication all to no avail.  Loading her old system off of a backup drive confirmed the settings and server were otherwise working fine, it was definitely a Mavericks issues.

The solution from Pismo-C here worked well although I have yet to test it over a prolonged period of time (to see if the server will block it again) although I doubt it will break due to it working well during a period of active testing where nothing else got through.  See screenshot here showing certificate trusted in Keychain Access

Thanks Pismo,

after months and months of different trys, this one worked for me !

Excellent tip.

Thanks