Unable to send mail using MobileMe after upgrading

I have exactly the same problem. I have tried deleting and re-instating my mobileme account, but so far (my mobileme account is still syncing) I still cannot send mail. Anyone else experience this?

It is specific to my mobileme account. Sending via an Exchange account works fine.

Tim

In your Mail's preferences, go to accounts and check yout outgoing mail server. My outgoing mail server authetication had been set "none" after upgrading to Lion. I reselected my old settings from the drop down list and I was able to send messages again.

My outgoing mail server authentication was fine.

I did manage to fix / isolate the problem though.

Turns out that after upgrading to Lion, sending mail via MobileMe defaulted to using digital signing. I've never noticed this feature before and to my knowledge had never enabled it prior to upgrading to Lion. For whatever reason, turning OFF digital signing allowed me to send mail again.

I also noticed something odd which had escaped me before. Before I discovered the solution of turning off digital signing, whenever I attempted to send a message from my Mobileme account, a very brief dialog box flashed across the screen. It was fast enough that I did not notice it at first. To actually read it required me to use Quicktime Player to do a screen capture, which let me freeze the frame where the message appeared:

Unable to sign message.

An error occurred while trying to sign the message with a certificate from "xxxxx@me.com". Verify that your certificate for this address is correct, and that its private key is in your keychain.

To my knowledge I have never set up a certificate, which could explain why the message would pop up. Why the dialog box flashes so quickly on the screen is still a mystery.

Now... time to read about digital signing, and certificates, to try and understand this.

Ok... read up on signing, certificates, and email encryption.*

After familiarizing myself, I confirmed that I had not previously ever installed a certificate for digital signing of email. At least, there was no certificate in my Keychain directly assigned to my email address. There was one, issued by Apple, associated with my Apple ID which uses the same email address, but I assume that is for AppleID logins only and not for Mail?

I then proceeded to download a certificate (from Comodo) for my email address, and install it in the Keychain. After doing so, I now became able to send digitally-signed email from Mail.app (ie, turning on the "digital signature" option no longer resulted in send failure).

It's not clear to me how or why the Lion upgrade caused digital signatures to be turned on by default. I suppose it is technically possible I accidentally clicked on it while exploring the new Mail.app, but I have no recollection of doing so.

Has anyone else experienced this?

___

*This seems to be a really poorly documented feature of Mail.app. Best links I could find date from the Panther OS 10.3 days:

http://support.apple.com/kb/TA22353?viewlocale=en_US

http://joar.com/certificates/

The removal of my mobileme mail account, quiting mail, then re-opening and adding my mobile me account again seemed to work for me; mail is now sending from my mobileMe acount again, although it still took an unusually long time (over a minute) to actually send the message. It just kept spinning.

Anyway. There are a few other glitches in Lion OS which is making me regret doing the update so quickly and blindly. I have spent hours trying to solve these problems... yeesh. Thanks for the post and sharing your solutions. Chris

I was having the same problem, for the past few days (Since upgrading to Lion) I have been unable to send email from my MacBook Pro. But I have found another solution that worked for me, without having to delete and then re-add my accounts.

After doing the upgrade to Lion, it turns out that the passwords that Mail saved to connect to the SMTP server(s) for my email accounts (MobileMe & Hotmail) were deleted. All you have to do is go into Mail > Preferences > Accounts > Account Information; click on the drop-down menu beside "Outgoing Mail Server (SMTP)" and choose "Edit SMTP Server List". Under the Advanced tab for each server, just re-enter your password.

Hope this helps!

I'm having the same problem and it's making me quite mad at Lion.

I've verified that on the Edit SMTP Server Liist, all passwords are in place. I don't know what to make of the certificate possibility.

Deleting the MobileMe account to recreate it is fairly major in that I stand to lose sent mail, etc.

Help, somebody.

There is an ongoing issue with the mobileme outgoing server....

https://discussions.apple.com/thread/3146283?start=0&tstart=0

Hang on to your hats. I imagine it's got something to do with the iCloud changeover.

Not very impressive really, espcially as they haven't even acknowledged it on the MobileMe homepage.

Bad job Mr Jobs.

I too has the same issue. Resolved by going into preferences ( mail ), account. Found there were 2 email addresses, pierre24@me.com and xxx@mac.com. Removed the xxx@mac.com and all works like in SL.

I think I have this figured out: I think MobileMe wants to be an IMAP account as of Lion.

In previous OSes, it could be either POP—the way my broken account was set up—or IMAP. Going all IMAP is perfectly consistent with the iCloud migration, too. It would also be kinda typical, if not helpful, of Apple not to announce this kind of low-level change for MobileMe now.

Ever since I deleted my MobileMe POP account from Mail and created a new one (Mail surprisingly made it an IMAP account by default), I've had no problems sending mail. It's been three days now.

I'm curious to know if others who are having this problem have their MobileMe Mail accounts configured as POP accounts.

I will say that deleting the old POP account and adding the new IMAP account didn't cost me my old Sent mail or anything; it was painless.

Thanks for this comment but how exactly do you turn off digital signing?

Aha. In the right hand corner of the "new message" mail window there are two small icons, one for encrypting messages, the other for digitally signing messages. If you have not set up digital signing (downloaded a certificate and installed it in your keychain), both of these icons should be visible, but grayed out. If you have set it up, the "digital signing" icon will become available. If you have set it up, AND you are sending your email to someone who has provided you with their public key, then the "encrypted" setting should be available also.

What was odd in my particular case was that after Lion, digital signing seemed to have been toggled ON. This is despite the fact that I had not, to my recollection, ever established a private key for my MobileMe mail account.

Yet, Lion was attempting to use one, and was complaining that the digital certificate it was attempting to use could not be read.

I could have fixed this just by turning digital signing OFF. But after learning about digital signing, it sounded like a pretty good feature, so I went to the trouble of obtaining a certificate & installing it.

Thanks my friend you are now officially my favorite person in the world!