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Apple Mail Sending Issues in Snow Leopard

Reports have surfaced that some Snow Leopard users are finding themselves unable to send messages from within Apple Mail, though they continue to receive messages. Upon attempting to send mail, many users receive an alert message that states, "Error 54: Connection Reset By Peer." Yet, not all users receive an error message; some simply see their message fail to send. Apple recently acknowledged this issue in a KnowledgeBase article, and suggested a couple of workarounds.

In the article, Apple explains that Mail in Snow Leopard (as opposed to Leopard) sends messages through a different port rotation for the "Default ports" setting, and thus some users may need to update their SMTP authentication settings for outgoing messages. The article goes on to provide information regarding how to do so, and, should this first option fail, how to change the port that Mail sends through.

However, back-and-forth on Apple's discussion forums indicate that Apple's suggestions aren't working for everyone. In a lengthy forum thread, some users have reported that calls to Apple indicate engineers are in the process of developing an update to resolve the issue - though Apple has not officially confirmed this. Such an update would likely ship with the 10.6.1 update, which, if past performance is any indication, should be available within a week or so.

Until more is known about this issue, there isn't much affected users can do beyond trying what Apple suggests other than switching temporarily to another email client for sending mail. That would be a terrible workaround unless you're using IMAP, at which point you could receive incoming message with Mail, wait until they were all filtered appropriately, and then read and respond in the other program.


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Comments about Apple Mail Sending Issues in Snow Leopard
(Comments are closed.)

Working Stiff  2009-09-03 15:01
Worked for me.
After installing Snow Leopard, Mail got "rejected" by my ISPs smtp server.

Resolved it by going to Mail Preferences, Edit Outgoing Mail Server, Advanced. Then change the radio button to Custom Port 25 (may be different # depending upon your ISP),
Authentication set to None. Click OK.
Good luck.
John Baxter  An apple icon for a Friend of TidBITS 2009-09-03 16:32
Not a problem here so far. But we alredy have our users specifying port 587 on new setups and any time we have support calls about email from them. (Regardless of mail client or plaform except very old Outlook Express.)
Curmudgeon Geographer  2009-09-03 20:13
How about the Snow Leopard Mail problem of not being able to delete RSS posts? Subscribe to an RSS feed in Mail, delete some posts, erase all deleted messages, quit Mail then restart Mail and you will find all your RSS posts back.

There is no way to make your RSS posts stay deleted in Snow Leopard's Mail . . .
Adam Engst  An apple icon for a TidBITS Staffer 2009-09-04 05:59
Hadn't heard about that one yet, but I can see where that would be insanely frustrating.
sevenof400  2009-09-07 18:45
I was able to delete the RSS feed in mail with no problem .. however, I did away with ALL RSS feeds. Do you have any RSS feeds that you want? Might try deleting them all if that's an option.
Peter Skinder  2009-09-15 14:56
I have to Apple related this problem as soon as I installed OS10.6 and they told me that it would be fixed on the next revision. OS10.6.1 came out but flaw was not corrected. I contacted them again and received the same promise. Every one should go after Apple so that they get of their but and make the correction now not some time in future as my Trash file is getting filled up with RSS that will not delete.
James McEwan  2009-09-18 08:39
Further to my comments of yesterday, deleted RSS feeds are reappearing again in Mail. Damn.
Sorry about any dashed hopes!
Matt Mann  2009-09-04 11:59
In my case, I wasn't getting an error message, the send button was simply grayed out and I could not click it. I went into preferences and discovered that somehow my outgoing mail server had been set to "none". I set it to the correct server and voila! Not sure why this happened, but seeing as it occurred right after the OS upgrade, that must have reset it. All better now though.
Sharon  2009-09-07 19:24
I take tech support calls. Apparently Snow Leopard's Default Ports won't accept Authentication None, and change it to Password authentication.

So far switching to custom port 25, Authentication none has worked for the customers I've talked to. Calls have dropped off, so apparently the word is out.

As much as I love Apple, their testing should have caught this.
I have my server at the default settings and it works fine, but be have port 587 (submission) enabled on the server.
H Polk  2009-09-08 06:34
I have both problems, Mail won't send and changing port to 25 works but it keeps changing to 587 and then won't send. I am using Cox.net as my ISP. Also RSS won't delete, so I deleted the feeds. Hope fix comes out soon.
warren rasmussen  2009-09-08 08:46
in mail, attachments and images part of my signature appear squashed. also when selecting attachment and then view as icon, message window goes blank.
Willie  2009-09-09 13:16
Every time I turn off my imac for a long weekend away from the office I come back to mac mail issues. I can send, but cannot receive mail. I can get it on my phone so that's how I know I'm able to send. Nothing has changed, I've checked the settings and completed updates and still nothing. next to my inbox and below where it has all of my folders under the heading of my email address there is an ! inside a triangle inside a circle. I've tried taking all accounts online but nothing happens. I'm not sure why this happens or what to do. Unfortunately, I'm the only one at my work that uses a mac so tech here is not helpful. Help!
Brian   2009-09-10 11:22
Just got off the phone with Apple support. I switched from Entourage to Mail (Exchange server) and have had issues sending large emails. Come to find out Mail will only send up to 20MB per email. Entourage is able to send greater than 20MB (it may take 2-3 minutes). This is a big problem for Exchange users with businesses as a lot of emails contain attachments etc greater than 20MB. Support said they did not know if there would ever be a fix on this. Anyone else see this? Back to Entourage I go....
My mail server caps attachments at 10MB, however, I know that I sent a 35MB movie with Mail app in the past. Is this a Mail.app restriction or limited to Mail+Exchange?

Anyway, 20MB is certainly reasonable for a mail limit. There are far better protocols for sending large files.
Brian   2009-09-10 14:55
My question is this, why would any business switch from Entourage that will send outgoing mail of all sizes to Mail which will limit the size of outgoing mail?
because large attachments in email are a horrible idea, stress mail servers, and are often rejected by the endpoint server. Like I said, my mail server has the cap at 10MB. 10-20MB is pretty normal.
gregg zulauf  2009-09-11 10:11
I had problems sending emails with macmail OS10.5. The problem, I discovered was changing the outgoing server name. When this new server name was saved, macmail would always open with SMTP server listed as 'none'. The fix was to simply click on none and choose the new server name listed in the drop-down window.
Whew! I would have assumed apple programers would have the save command place the newly input server information as the new default - it does not.
Note that effective 15 September, Verizon has shut down port 25 on their networks, and is requiring you use port 587 at all times. There is still some question whether they are also blocking direct access to ISP's or whether you have to relay through their servers with the return address set to the 3rd party email address.
Laurens Wildeboer  2009-09-30 14:30
the upgrade to leopard has given me a lot of grief with mail and my iomega backup drive. Mail sometimes sends, sometimes receives etc etc. I deleted the mail settings in an attempt to rectify the situation, lost all my mail and set up new mail boxes (as recommended) and the same problems still exist.