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September 2, 2009 9:28 AM PDT

Troubleshooting Mail issues in Mac OS X 10.6 Snow Leopard

by Joe Aimonetti
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Various reports have surfaced around the Web regarding unexpected behavior of Apple's Mail application in Mac OS X 10.6 Snow Leopard, prompting Apple to release a knowledge base article describing possible troubleshooting steps for the program.

MacFixIt reader "Gerald S." reports:

"After upgrading to Snow Leopard, I can no longer send mail. I have a clue, though. The issue seems to be related to existing mail accounts. If I create a new mail account, it works just fine. Now we need to figure out how to import older mail into a new account."

If you are having issues sending Mail in Snow Leopard, you may need to update your authentication settings for your outgoing mail.

Users should follow Apple's Mail Setup Assistant or contact their ISP to determine the proper settings for their e-mail service.

After obtaining the proper settings for your mail account, Apple suggests these steps:

  1. From the Mail menu, choose Preferences.
  2. Click Accounts, then select the account that is having issues sending messages.
  3. From the SMTP server pop-up menu (at the bottom of the window), choose "Edit SMTP Server List".
  4. Click Advanced.
  5. Select the 'Authentication' pull down menu and select the appropriate authentication type (from your ISP or the Mail Online Setup Assistant).
  6. If necessary, fill in the username and password.
  7. Click OK
For more on troubleshooting Mail in Snow Leopard, read the entire Apple KB Article.
Joe is a seasoned Mac veteran with years of experience on the platform. He reports on Macs, iPods, iPhones and anything else Apple sells. Before joining CNET, he even worked in Apple's retail stores. He's also a creative professional who knows how to use a Mac to get the job done.
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by snapessecret September 2, 2009 8:08 PM PDT
Apple Support advised to use the SnowLeopard install disk and install mail as a separate app, after the upgrade to 10.6. This solved a bunch of problems related to repeated requests for keychain verifications, loss of mail account password information and inability of mail to retain newly installed passwords. The separate install of the mail.app also seemed to clarify links to the address book and ical.
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by Jon September 3, 2009 8:22 AM PDT
After scouring the Internet for a solution to the (unbelievable) problems created in Mail and Address book by the upgrade to Snow Leopard, (and I actually PAID for this grief????), I stumbled upon this solution and it actually seems to have relieved the symptoms: hundreds of duplicate messages, missing mail, unable to retrieve mail from servers (IMAP AND POP), eventually the mail application crashed every time I tried anything at all, eventually unable to open Mail;, address book multiple entries (tripple +), horible synching difficulties, etc.

Address book in Mail still does not reflect the Address Book application accurately. The sort order does not work and "No Name" appears in addresses that are filed under Company Name (Company Name is omitted in this view from Mail). Very very buggy stuff. What a feasco.

I've never had this kind of problem with any upgrade from Apple before. it's unacceptable by any standard (except perhaps, Windows). I expect Apple to be above releasing such buggy, almost Beta, software . . . and then to actually CHARGE me for it! Not good. Not good at all. After reinstalling the separate Aps from the Snow Leopard disk, most of the problem were resolved. However, the address book is still buggy and mail occasionally crashes for no apparent reason, randomly. I'm very disappointed in this "upgrade".
by Swirlingeddy September 12, 2009 7:34 AM PDT
Jon - I have the duplicate messages problem, big time. What did you do?
by toddalbert September 2, 2009 9:52 PM PDT
Problems with Mail may drive me back to 10.5 for now. I have little trouble sending or receiving mail, but opening the preference pane (I almost spelled that "pain") almost certainly leads to the program becoming unresponsive. The application seldom quits for me without being forced, whether it has been frozen or not. I've sent many bug reports to Apple, and my account settings seem to be fine (although I can't really check them out to verify).
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by jshawnl September 2, 2009 11:05 PM PDT
Two annoying quirks in Mail that arrived with Snow Leopard:

1. Copying an address used to copy just the email address. Now it copies the whole name in the form "FirstName LastName <email@address>" . This makes it virtually impossible to copy email lists anymore. Who thought this was an improvement?

2. Mail can't seem to handle changing font typefaces when it would switch from one font to another (e.g., regular to italic, or regular to bold, or regular to bold italic). Switching from regular to underline isn't a problem, perhaps because it isn't a typeface switch?
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by jcds83 September 2, 2009 11:08 PM PDT
I had a lot of problems with Mail after installing SL(authentication of the pop accounts and display of messages not functioning).
I solved the display problems by deleting all things related with the bundles deactivated by SL in my pref plist of Mail.
For authentications problems, I added the port 25 in my smtp settings.
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by OurShop September 3, 2009 2:52 AM PDT
"I solved the display problems by deleting all things related with the bundles deactivated by SL in my pref plist of Mail."

Where is this sorry?
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by nance2key September 3, 2009 10:33 AM PDT
hate to say it...but the problem w/ inability to send mail w/ the Mail program is not new..i've had a mac.com account for years and .although i can receive mail, i have never been able to send mail thru the program. To be honest-i haven't ever made the attempt to fix the issue because im busy and lazy...and can bypass the issue by going online to pick up my email.
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by EX-applefreak September 3, 2009 3:04 PM PDT
After downloading Leopard Mail version 4 did not even start up.
Non of the view available net support solutions did work.
Including failure of apple trouble shooter site for 10.6 mail problems!!!

I think IŽll buy a window thing, then I know iŽll be in for trouble anyway.
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by daniel_garceau September 3, 2009 4:37 PM PDT
Mail would not work after installing OSX 10.6
My accounts info would not remember the passwords for each account and keychain kept reporting an error in accessing the keychain.
Deleting the keychain "session" (links and files) and restarting (forces OSX to recreate a new session keychain). Add to put in the accounts passwords again and then everything went back to normal.
Of course deleting the session keychain means that I will be asked to confirm access to the keychain at least once everytime something wants to access the keychain for the first time but that is a small price to pay. Maybe better solutions are around but that worked for me and may be helpfull to someone else
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by jshawnl September 3, 2009 10:20 PM PDT
Update on the issue changing font typefaces: turns out that Mail doesn't know what to do when there are duplicate fonts in various font folders, *even* when one of the duplicate fonts is disabled. Deleting all the duplicate fonts makes the problem go away.
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by JapanDan September 4, 2009 7:58 AM PDT
I'm having some really weird problems with Mail 4.0 in Snow Leopard.
1)Beach Balls everywhere - almost every time I click between inbox and other mailboxes, I get a beach ball for as long as a minute
2) Occasionally the message count at the top of the window is way off, for ex. - "INBOX(189,210) and I have only 450 messages in that box. I tried creating a new mail box, and moving the 450 messages from the INBOX to the new mailbox, and the message count was correct. I then moved the messages back and the problem was resolved - EXCEPT - it returned. It is a problem that only occurs occasionally.
3)AND THE MOST ANNOYING, EVEN MORE ANNOYING THAN THE LINGERING BEACH BALLS IS - Mail won't quit. It occasionally does after a long time, but it almost never quits.

I have rebuilt the database by dragging "Envelope Index" and the folder RSS from ~Users/XXX/Library/Mail/ to the trash and restarted Mail. This imported the mail messages and the problems got slightly better.
I switched the Check Mail option to check mail manually.
I turned off Time Machine.
I ran Disc Utility to repair disk and repair permissions.
I only have two accounts turned on, my me.com account and my main email provided by my cable company.
I deleted all messages off the servers.
I tried turning each account off to see if it was the problem, no change.

Any ideas.......... anybody???
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by JapanDan September 4, 2009 8:05 AM PDT
Can this be done with the update disk as well? That's all I have. I looked through the CUSTOMIZE INSTALL options, but I didn't see a place to install mail only. Do I need to delete the mail.app before I startup with the install disk for that option to be made available?
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by radius11 September 6, 2009 9:29 PM PDT
As far as I understand, the update disks have the whole nine yards on them, and are not simply an update.

On the lead screen you get when you put the Snow Leopard disk in, go to Optional installs >> Optional Installs.mpkg. After the regular license agreement, and selecting the install drive, under the Applications you will find all standard OS X applications, including Mail.

The issues are just surfacing on my Mail application. Can send mail to some addresses, not to others. Sometimes I can download messages, as time goes on, more often, not.

Ray~
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by 500sl September 18, 2009 9:09 AM PDT
When starting the Mail application, I have the beach ball for 24 hours (two-four!). After that, everything works fine. Hardest thing is to remember not to close Mail... Any ideas? Tried everything from deleting caches to repair permissions.

BTW: Same thing happens with Address Book

500
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by fangoo September 19, 2009 8:36 AM PDT
Im having a problem with Mail in Snow Leopard. When I select "save all" attachments, Mail frequently crashes - but not always. It can work for a while but inevitably it eventually crashes. Some all or none of the attachments may be saved. If i reopen Mail and try the same thing it usually works.

Anyone else? I have noticed that saving attachments is instantaneous - when it works. In 10.5 it took 1 second per attachment to save.

I like Snow Leopard but I seem to have a few kinks...
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by clogz14 September 21, 2009 5:36 PM PDT
Thank you people for providing this info I have posted the link in the Apple Forum.
I solved my problem half I have a brand new account with my provider now sending out messages as well.
BUT VER SLOW REACTING not at all as it was in 10.5 SL appears to stand for SLOW LEOPARD
an UUE ( Unbelievable Unacceptable Error) pay money to test a program!!!!
thanks for you info
clogz14 New Zealand
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by BusinessWorks September 23, 2009 1:24 PM PDT
To eliminate the SMTP send errors in most cases for SMTP accounts that DO NOT require authentication, unselect the default ports setting on the account and then select custom port and enter 25 as the port number. Apples SMTP problem seems to have something to do with attempting to use the other ports in the default list (it might be the order in which the ports are tried or it could be that the SMTP server rejects unauthenticated requests on these alternate ports.
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by swross October 6, 2009 8:38 PM PDT
Since upgrading to 10.6 Snow Leopard, mail set to be pushed to my iPhone (via a rule) is getting send randomly by the hundreds.
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by Nigel_Davenport November 4, 2009 4:47 PM PST
OK.....here goes.
I could receive mail but not send same.
Look under Mail. Go to Preferences.Look into Account Information under Accounts.
The Outgoing Mail Server (SMTP) drop-down bar MUST be set to NONE. This will automatically default to the right ISP setting if you have filled in the previous account information.
Then check the box that reads "Use only this server"
Bob's your uncle.
The very second I did this, all messages in my outbox were sent one by one.
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by Victor_R November 9, 2009 11:04 PM PST
Wow - With several on here if we put our systems together we are set...
I can send, but cannot receive -
More pain after 5 remote-Re-installs, internet functions, Mail is set up, can send to anyone, anywhere -
But, cannot receive... Help - please :)
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