Mountain Lion Update - Mail (SMTP) Offline Ever Since

I discovered this behaviour just after upgrade to OS X 10.8.4 - on 3 different machines (two iMacs - at home and at work; and one MacBook). I played with Keychain, removed password, certificates, etc., but nothing helped. Then I found a solution for me:

First of all, my situation is that I use my employer's (university) smtp with SSL on port 465. In the settings of this smtp, there's a tab "Advanced" (I'm not sure with exact English translations here because I use localized OS X, but I guess you can get the meaning). This tab has couple of entries like dropdown menu "Authentication type" (here I have "Password"), fields for username and passrowd, checkbox "Use SSL" (which I have checked) and two radiobuttons: "Use default ports (25, 465, 587)" and "Use own port ___". The problem was with these two radiobuttons... normally the first one was selected and I believe that prior to the 10.8.4 upgrade it worked fine and Mail was able to figure out the correct port. However, after the upgrade, I had to choose the second option "Use own port ___" and manually write 465 there. So this actually helped me and this smtp works again.

However, there was another glitch after I fixed this one: when I ran Mail the next day, this smtp didn't work again. So I checked these settings again and found out that there was the incorrect port number 25 again instead of 465: I don't know why, looks like a bug or something. I changed it back to 465, it works again, I restarted the computer just to make sure, and 465 still there and smtp working. So I hope it will stay like this.

I was having a similar problem with one of my four email accounts. The other three accounts worked fine, but one was "Offline." In my case, when I checked the "Edit smtp server" list in Mail preferences, the password field for the smtp server was empty. I'd re-enter the password and click "OK," but the password wouldn't stick. If I opened that server's settings again, the password field would be empty again.

I called Apple Support, and they had me go into Keychain Access and delete the Keychain item for that smtp server. (Just the one for the smtp server, not the one for the incoming server.) Then we went back into Mail preferences and re-entered the password, and that fixed it.

I'm having this exact same problem after updating Mountain Lion at the last update - it's shocking that a fundamental app is broken. Tried the above suggestion without success...could you give a bit more detail about how you fixed it?

Further to this - my smtp setup works fine on my ipad and iphone but suddenly stopped working on my mac post Mountain Lion update. I've had to use the gmail smtp server in mac mail as a temporary fix. Any updates on how anybody fixed this would be appreciated... 😠

Here's how to see if you're having the same issue I was having. (Note that, for me, the problem was not with my iCloud account; I don't know whether the steps below apply to fixing this problem for an iCloud account.)

1. In Mail, go to the Mail menu and choose "Preferences...".

2. At the top of the Preferences panel, choose "Accounts."

3. In the sidebar, choose the account that you can't send from.

4. At the top of that account's panel, choose the "Account Information" tab.

5. Go down to the "Outgoing Mail Server (SMTP)" dropdown menu. Does the affected account's smtp server have "(Offline)" next to its name in the dropdown menu? If yes, choose "Edit SMTP Server List..." from the bottom of the dropdown menu.

6. In the middle of the panel, choose the "Advanced" tab.

7. Can you see a Password field? If yes, is the Password field empty? If yes, then fill in the password and click "OK" at the bottom.

8. Now, as you did in Step 5, choose "Edit SMTP Server List..." from the "Outgoing Mail Server (SMTP)" dropdown and click on the "Advanced" tab. Is the password field that you just filled in empty again? If so, you're having the same problem I was having.

Here's how we fixed it on my computer:

9. Open your Applications folder. Find the Utilities folder and open it. Open the Keychain Access application.

10. In Keychain Access, in the panel on the left side of the window, click on "login."

11. In the main part of the window, in the list of keychain items, locate the keychain item for the mail account that's not working for you. Its name will likely start with "smtp" (as in, for example, "smtp.gmail.com") or it's possible that it could start with "mail" (for example, "mail.pretendemailservice.com").

12. When you find the keychain item for the offline smtp server, click on it once to highlight it, then go to the Edit menu and choose "Delete."

13. Now go back to Mail preferences and enter the password in the same place you tried to enter it in Step 7 above.

In my case, this fixed the problem. The password did not disappear after I clicked "OK," and I was able to send email from the account again. I hope this works for you. I know how maddening this problem is.

Hello,

I have the same smtp offline problem (OS 10.8.2) but it happened all of a sudden, it worked fine till yesterday. The difference for me is that the password in the advanced tab is there and there is no way to get the offline out, i tried wiping it out from the keychane and putting it back in, changing the ports to custom port n.10 that some says worked. but nothing seems to work for me, have any idea?

Mine was the same. It was working fine, then, out of the blue, it stopped working for no apparent reason. It wasn't related to any kind of an upgrade, as far as I know. I'd been using Mountain Lion for a while.

I suggest calling Apple support. That's what I did. The first person I spoke to walked me through all the most obvious troubleshooting steps, and when it became clear that he couldn't figure it out, he passed me on to someone he referred to as a "Mail expert," and she was able to figure out the problem pretty quickly.

Hi Chaps,

This issue can be caused by a bug in ML allowing a space in your local hostname.

Navigate to System Preferences>Sharing. You will see your computer name on the right.

Click edit to edit your Local Hostname. Make sure there are NO SPACES!

😉

I just want to throw in my support for Mac User Since 1993's solution. Seems to have cleared everything up for me. I had five accounts unable to send mail. After deleting their password entries in Keychain (quit Mail first), then re-entering them in Mail, everything got cleared up. Thanks a lot!

I, too, would like to thank Mac User Since 1993 for their solution. I upgraded to Mountain Lion 10.8.3 from Snow Leopard 10.6.8 the other day and immediately ran into this SMTP (Offline) problem after enjoying years of using Apple Mail to manage my AOL Mail -- It was driving me crazy! Deleting the Keychain items linked to the smtp part of my email solved the problem for me, and all is well again.

I tried mac user since 1993... to no avail I still cannot send email from the mail application. This is really frustrating. I have already been to the Mac store once. I have tried everything suggested in this forum 3 times. the account is still going offline and no mail is sent.

Help!

KM

Great discussion about a frustrating Mac Mail problem. I am experiencing this issue and went through the steps above. After deleting SMTP from the keychain and entering a new password, the "(offline)" text disappears for less than one second but then comes right back. Looks like I must spend a little time on the telephone with Apple to get this resolved. Hopefully the next software update will resolve this.

I am also having the same issue on my two email accounts. One is blueyonder and the other is btinternet.com. Both show offline. I have deleted them from the keychain. Deleted the accounts from mail and set them back up. All to no avail. Hopefully apple will find out what they have done and fix it.

@rompi : Yeah, tried the SSL with port 465 to no avail. Just using my iPad for outgoing mail just now until Apple get this fixed. Also tried removing SSL and changing ports, none of which worked unfortunately. Still showing servers offline and still unable to send emails from my iMac

I too have been bitten by this bug. Any attempts to get the POP account to work after changing SMTP server settings would result in the server SMTP showing as offline. It would not even receive email and the account would show offline in Mailboxes listing.

I had to change the user credentials of the original email account to a bogus one so I could add a new one using the original email account. Otherwise it said the account already existed. After doing that everything worked after adding it as a new account.

This had to be done on all the POP accounts where the servers changed and then move all the emails from the original renamed one.