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Unable to send mail using MobileMe after upgrading

Since upgrading to Lion I can no longer send an email using my MobileMe account from my MacBook Air (11"). Mail spins aways for several minutes trying to send the message before finally displaying a pop up that the mail couldn't be sent using a standard port. This worked fine in Snow Leopard.


Sending from my upgraded iMac on the same MobileMe account works fine. What is particularly odd is that I have the mail accounts set to sync across the machines using MobileMe. So the settings are identical. Both machines are connected to the same router (Airport Extreme). The iMac via Ethernet and the MacBook Air via Wifi.


When I run Mail's Connection Doctor it says Connection and login to the server succeeded. Yet of course it can't connect to send mail. I can receive MobileMe mail just fine.


Any ideas how to resolve this?

iMac i5 27", 8GB RAM, Mac OS X (10.6.5), also 11" MacBook Air, iPhone 4G,Mac Mini 2.26GHz, 2x Apple TV

Posted on Jul 23, 2011 6:19 AM

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47 replies

Aug 4, 2011 4:01 AM in response to PRP_53

There may be no need to delete accounts as per the above suggestions (and even noted "correct" answers)...


I had two issues :


1/ had to replace my password for the SMTP server for each user on the machine. that got everyone going but me.

2/ for my account to work which was the only one on the machine that had two listings as P Phillips notes, had to remove the double account listing

Aug 4, 2011 7:25 AM in response to timyu

This way worked just perfectly for me. I was having the same issue where there's a pop up too fast to read when trying to send any mail from my mobileme account (by the way, sending through iPhone always fine). I have noticed the new certificat sign on the corner bt never thought it's the cause of the problem.


Anyways, I have turned it off for the new message, and it stays off until you turn it on again, even for new messages.


Thanks for the help.


BTW, removing the account, quitting mail, re-adding the account again did not work for me initially.

Aug 14, 2011 11:52 AM in response to timyu

OK I have just experienced the same certificate issue with a gmail account, not a mobileme account. I've been looking for the thread that says - 'OS X Lion - unable to send mail on one gmail account, quick error message flashes and message stays in drafts'


SO as it turns out with Lion we can add an Apple ID to our User Account. Well, when you do this, Lion creates a certificate in your Login keychain identifying you, and if you happen to have an email account using that address it somehow relates to this certificate now. Worse for me, I installed Lion fresh on a new HD and so I had imported a keychain from my previous SL system, which had some useful passwords in it.


WELL, Lion created my 'Apple ID' certificate in this temporary added keychain, so when I removed that keychain from my system, the certificate went with it and mail started complaining. Same error as above, only mine was with a gmail account. Worse AGAIN for me I have like 5 gmail accounts in Mail, all with IDENTICAL settings and THIS one (my primary email, naturally) was the one failing.


THE FIX:

I did all these steps to fix it but you like don't have to do all of them -


1) Quit Mail

2) System Preferences -> Mail, Contacts, Cal --> remove all (gmail) accounts

3) Open Keychain Access from Applications/utilities, browse to login keychain, all items

4) System Preferences -> User Accounts ::: Remove the Apple ID, see if your apple ID cert vanishes

5) ~/Library/Preferences/ ::: move/rename/delete com.apple.Mail.plist and its lock file if present

6) System Preferences -> Mail, Contacts, Cal --> add your problematice email account back, test it out.


That cost me about 48 hours 🙂


Also- for the screenshot I went into System Preferences -> Keyboard -> Keyboard Shortcuts and changed the shortcut for full screenshot to file to Alt+Z so I could quickly snap a full screenshot of the error message that timyu mentions above. Saved a PNG to my desktop, which was what ultimately led me to find this post.


What was dissapointing was the fact that this error wasn't logged in the system log anywhere that I could see in the Console app.

Aug 16, 2011 9:23 AM in response to Ron Guest

I had this issue as well and fixed it via a simpler method. It seems that with Lion, the SMTP server defaulted to smtp.me.com but per Apple ( http://support.apple.com/kb/ht1625 ) .mac accounts should use smtp.mac.com.

Since I was trying to send via the smtp.me.com with a .mac account, it was failing. I changed the server to smtp.mac.com and everything works well.

Aug 16, 2011 11:16 AM in response to Ron Guest

I have been having this issue intermittently for a while. I couldn't figure out what was going on since it would come and go.


I came here to see if there are any answers, and I found one myself that seemed to do the trick. Hopefully it will help others.


1. While in mail go to the top menu and click on Window --> Activity

2. This shows all the different activities mail is involved with (ie. connecting with servers)

3. I found that I had 2 activities stuck - both trying to connect to the smtp.me.com server

4. Next to these activities is a big red stop sign. When you click on them they disappear.

5. Go back to your outbox double click on the email you are trying to send and hit send again.


For me this fixed the problem immediately and I was back to sending my emails. Hopefully this helps someone.

Aug 17, 2011 3:09 AM in response to Ron Guest

I found a fix that is completely different than all of the above. I hope that it helps some of you that were still having issues sending mail after trying those solutions.


FIRST CLOSE MAIL.. then,


1. Enable your ability to view your "Library" folder by opening the program called "Terminal" and pasting the following code: chflags nohidden ~/Library


2. In your hard drive/finder, go to users/yourusername/Library/Mail/V2/MailData


3. Locate "Accounts.plist" file. Right click on the file and choose "open with Text Edit"


4. With Text Edit open, hit "command F" on your keyboard to find the following words: LastSuccessful


5. Just below this line, you will see <integer>some-number</integer>


6. replace the number with 587 (this is changing the outgoing port for smtp)


7. close the Text Edit window.


Try sending a message now... see what happens. Let me know if this helps.

Aug 24, 2011 10:16 PM in response to magyarmerce

As another option, you can go into the Mail preferences menu. Under accounts, select your .Mac/MobileMe account and then click the pop-up list of outgoing mail servers. Pick "edit smtp server list" In the new window, find your .Mac/MobileMe account. Click it and then click the button for "Advanced" Here you can pick a custom port versus the top radio button. I used "587" in the custom port and saved everything. This fixed my problem about sending email instantly.


Nice catch. I would have thought using default ports (which includes 587) should work, but something in Lion (or forthcoming) iCloud must've broken. Just glad smart people found a fix! :-)

Unable to send mail using MobileMe after upgrading

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