Apple Mail logoLast week I looked at a few potential pitfalls to watch-out for when installing Snow Leopard and asked you to report any new ones you'd discovered. Overwhelmingly, you identified Apple Mail as the main causality with many users reporting they either can't send anything (some receiving the message "Error 54: Connection Reset By Peer") or that it simply crashes on opening. How on earth Apple didn't test this is not clear but as some of us at Softonic think, maybe they just presumed only dinosaurs use a Mail client nowadays ;)

As regards sending problems, it may not be Apple's fault however. It seems that it could be related to a SMTP issues specific to different ISPs. Obviously, there's no way that Apple could have tested Mail with every ISP in the world beforehand. One Apple forum user explains:

With some ISP, notably those that are cable, the SMTP is not separately authenticated, but rather is trusted based upon the IP address of the Modem they provide you. For such ISPs and SMTP, the authentication must be set to None, and no password or username enter for the Outgoing Server. It is simple for Mail to guess wrong about this, and you must set it right in the settings for the SMTP.

However, other uses have reported that changing SMTP settings still hasn't worked for them. Here's a collection of suggestions to help you get Mail working again:

Update SMTP Authentication

This is Apple's only official response on issues related to sending problems. Go to the "Mail" menu and select "Preferences". Click "Accounts" and then select the account the one having problems. From the SMTP server pop-up menu at the bottom choose "Edit SMTP Server List". Click "Advanced" and then select the "Authentication" pull down menu and select the appropriate authentication type (from your ISP or the Mail Online Setup Assistant). Fill in the username and password and click OK.

Edit Outgoing Mail Server

Go to "Mail"  and "Preferences" and select "Edit Outgoing Mail Server". Select "Advanced" and then change the radio button to Custom Port 25 (depending upon your ISP). Se the Authentication to "None" and click OK.

Move Mail folder to desktop

Sounds simple but apparently it's worked for a number of users. Locate your mail folder in "/username/libary" and then move it the desktop. You can then import your mail messages by going to "File" and then "Import" and browse to the Mail folder on your desktop. You may find your mail is a bit disorganized after importing but you'll just have to put everything back in it's right place and folder manually.

Repair Permissions

Ideally this should be done just before and after your upgrade to Snow Leopard. If you've already upgraded however, you'll just have to use Disk Utility to repair them afterwards.

Use Time Machine

If all of the above fails, then just use Time Machine to rollback to reliable old Leopard.


  • Brunsky |

    Hi, I solved this problem using the Apple official response and it did work very fine. Thanks for the information.

  • Nicholas Mead |
    Nicholas Mead

    Glad it helped! I think as regards sending problems, Apple's solution seems to be working for most people (although not all it seems). The problems related to crashes though are more difficult to solve.

  • Jen |

    I've tried all of these and still can't get mail to work at all. This stinks!

  • FrankieP |

    I'm having problems with mine in that it won't connect to the servers at all to receive mail, let alone send.. nothing has worked so far, such a pain in the ar$e!!! Any other tips?

  • Nicholas Mead |
    Nicholas Mead

    That's a new one FrankieP. I'd roll back to Leopard for now if you need Mail desperately. It seems it's going to take Apple a while to address all of these problems.

  • Trevor |

    Nicholas, Hate to sound like a complete newbie (even though I am). Installed SL now it crashes CS3 Illustrator, mail when I attach things. VERY happy to go back to Leopard via Time Machine if you could give me a quick pointer on how to do it. Sucked in and trusted Apple that things would have worked. Didn't trust Microsoft and now the other side lets me down. Yes, of course I should have waited. I know, I know.


  • Nicholas Mead |
    Nicholas Mead

    Sorry to hear that Trevor - it seems Apple really haven't done a particularly good job of warning people about this. I could maybe understand if it was a revolutionary new OS but Snow Leopard is effectively a "major tweak" of Leopard.

    Anyway, to revert back to Leopard, you'll need to boot directly from your Leopard install DVD but rather than choosing to install it, just go to Time Machine in the applications menu. Select the last backup you made with Leopard and your system should revert back.

  • Owen |

    Try this too:

  • Owen |

    Whoops Maybe the URl will come through this time: http://discussions.apple.com/thread.jspa?threadID=2131375&tstart=0

  • Owen |

    There is a discussion on Apple Support that has a solution that worked for me. Has to do with having a smart group in address book that crashed both address book and mail.

    In case my URL does work search for this: Topic : Mail crashes bifore loading mails


  • Rod |

    Here's a poser vis-a-vis Mail (OSX 10.6.1): Now, my normal outgoing server rejects my password, a server/password that I've used for years, and I'm using their recommended port and password authentication (I've double checked with them on this), but if I use my comcast SMTP server with their recommended port and password, mail zings right out the door. No SSL either. Really strange. Any suggestions?

  • Rebecca |

    I just installed SN and when I use spell check, it crashes every time? I'm going to try the Apple fix suggestion above, but wondered if anyone else experienced this. Also, sending mail is v-e-e-e-e-e-r-r-r-r-r-r-r-y-y-y-y-y-y slow.

  • Rod |

    The more I try to use Mail, the more puzzling it becomes. There used to be a handy way to trash everything in the Junk folder, e.g., cmd-option-j. I can see it in the Mailbox pulldown menu, but it's shaded, i.e., inaccessible. In addition, I'd used the Trash box to throw stuff away that wasn't Junk (the Trash box was handy in case I changed my mind), and now that's gone. Perhaps, these features are still there, but I've given up trying to find them. Anyway, I think you're right: Apple must think users who still use mail clients are dinosaurs, and they've implemented these frustrating "improvements" to drive us into the clouds.

  • Nicholas Mead |
    Nicholas Mead

    @Rod, that's definitely an odd one. As mentioned previously, it's probably something to do with a conflict between some ISPs and Snow Leopard but it's still not clear exactly why these kinds of mail server problems keep happening.

  • Becks |

    Thanks Nicholas! I could get mail, but couldn't send... Just about drove me around the twist.

    Very simple and easy to use instructions, I changed over to port 25 and it just all worked like a charm.

  • Rod |

    I stumbled onto a small "restore" (not one of the big problems, e.g., the SMTP issues, however, but something): I've found the Trash box. To get it back, you can either hit cmd-5, or as an alternative, under the Mailbox menu bar > Go To > Trash. That should restore the Trash box and icon to the left column (under MAILBOXES), so once again, you can simply drag mail that isn't junk into the trash.

  • Maria |

    After installing Snow Leopard I could still send in my mail but not receive. I would get a message about the inbox timing out, no matter what port was entered in advanced preferences. I can receive my RSS feed in mail though. Any suggestions.

  • Rod |

    Addendum to the "Trash" box (above): Well, it's not exactly a full restore. Yes, you get the Trash box back, but no, the trashed mail goes away immediately, i.e., you're not offered a second chance to pull it out of the trash. Oh well. I'm thinking of switching mail clients unless or until Apple deigns to pay attention to us dinosaurs. ;-)

  • Steve |

    I just installed 10.6. In Mail, I can't select entire messages when searching. It's grayed out. The other options work.

  • Aldo |

    After installing SL, I could not download mail (timeout, also had issues with Safari). I read somewhre to force mail to start in 32bits mode. Application -> Mail -> Get Info -> click on the 32 bits mode.

    Solved mail and safari issues.

    Hope it can help....

  • Arla |

    Having same mail trouble w/SL. I cannot send any email. I get an error message that says, "The sender address Lu2plus2@cox.net was rejected by the server smtp.west.cox.net." I cannot change authentication to "none" as it is not a choice in the pull down menu. I AM VERY FRUSTRATED! Can you help? Thanks!

  • Jef |

    Tried all sorts of combinations: password, SSL, usernames, on/of, you name it. Sometimes it works, then back again not. After changing the custom port to 25 and turning SSL and authentication off, all works back again.

    ...And after a while I changed the MF to 32 bit mode too. Crossing fingers!

  • john |

    This is the most informed forum i have found on this subject. Has anyone had this problem or have any ideas how to resolve it. two weeks ago i accidentally clicked on something in mail 4.1 under snow leopard 10.6.1 i got a brief dialog box saying something about "connecting to server" this was whilst i was syncing mobileme with my old @mac.com mail account

    Since then i can't receive any incoming mails except from the apple news RSS feed these are getting through.

    i can send emails to myself from my mobile me account on the web from myname@.me.com to myname@mac.com the account i have always used before SYNCING WITH mobileme i can also send mails from myname@me.com to myname@mac.com

    thesee show up in mobile me and on my mail application 4.1 on the computer

    emails to myself from myname@mac.com via mail 4.1 to either myname@mac.com or myname@me.com do not get through

    and i can send out mails o.k from either mobile me on the web or via mail 4.1 on the computer.

    the incoming server name stmp.me.com is greyed out in the preference panes and so is the port number.

    i have followed the apple support instructions and screenshots but i am unable to edit the greyed out bits of the dialog boxes like apple suggest. they are unresponsive to mouse clicls.

    any help greatly appreciated i know i have a large backlog of incoming emails to shift through i just don't know where they are or how to retrive them

    thanks in advance john

  • Ben |

    I had a crash this morning. Luckily I can access my email via webmail too. It turned out to be a SPAM message that was causing the crash. After deleting it via webmail I could open Mail and receive the other emails without a problem. I tried to report this issue to Apple, but could not find an email address on apple.com to send my report and the SPAM message to. The SPAM message is still in my trash on webmail, so I can still send it.

  • Victor |

    Help- I have Mac-mini server, Snow Leopard 10.6.2 - recent install (new server, after 5 re-installs) - cannot get mail functioning... can send to anyone anywhere, but not able to receive anything from anyone - This is driving me insane!

  • Chet Kaplan |
    Chet Kaplan

    Add one to the Mail problems. Mail opens fine. The problem is when I try to attach a file, while searching for the file to attach, mail just crashes out.

    A warning to about print drivers, we have a Konica Minolta network server and it took me two days get 10.6 to see it.

    I've noticed we're up to 10.6.2 already. Very unlike Apple to send out a new OS this buggy. I have not seen a buggy release like this since 9.1!

  • Kerry |

    I'd love to roll back to Leopard using Time Machine, but, Snow Leopard screwed that up to.......I feel like a PC!!!

  • stuartt |

    I am also having a problem with spellchecking in Mail, if I hit the change button I get the beach ball of death and have to force quit the application. Any ideas ??

  • Nicholas Mead |
    Nicholas Mead

    That's a new one Stuartt. I can only suggest reinstalling Mail if possible.

  • Jo Hammond |
    Jo Hammond

    When I try to send mail, it takes A-G-E-S. I never had this problem before installing Slow Leopard.

  • Rob |

    I am having a weird problem with the to do app in my mail program. All the To Do's are in there but they are in a grey color and I can't DO anything with them. Also, when I try to create a TO DO from an email it shows when I right click but won't let me choose it.

    Anyone know how to fix this? I have been trying just about everything I can think of.

    I have the new iMac and using Snow Leapord (of course!)

  • jason |

    I'm having the same problem as Rob:

    All the To Do’s are in there but they are in a grey color and I can’t DO anything with them. Also, when I try to create a TO DO from an email it shows when I right click but won’t let me choose it.

    Has anyone found a way to fix this?

  • James |

    This past week I made a long overdue upgrade: from a G4/733 running 10.4.2 to a MacBook Pro 2.66GHz running 10.6.3. I moved the Mail Preferences and Mail folder to their appropriate locations on the new Mac. I launched Mail (version 4.2) and made the necessary tweaks on Accounts so that Connection Doctor showed green radio buttons for the Incoming and Outgoing Mail Servers on all my email accounts. Mail is receiving email perfectly in all my accounts (POP and IMAP).

    However, when I send an email, the Activity window briefly flashes, then goes to blank. Not only is the email not sent but it is nowhere to be found. I have even saved an email to draft before sending, and it disappears altogether after clicking Send.

    I wrote and sent a number of emails the first day of working with the MacBook Pro, not realizing what was happening until midnight. Since then I have been rewriting the emails and sending them from Thunderbird as I remember the various emails that I wrote, most of them work related.

    I have been searching for possible solutions but have found none so far. Has anyone reading this forum had the same experience? Any suggestion as to what the cause of the problem may be and what solutions I should pursue? Like I said, Connection Doctor shows everything working fine, but emails are not sending and completely disappear after the attempted Send. (I have performed all the standard procedures... restarted the computer, relaunched Mail, repaired Permissions...)

    With thanks, James.

  • Tongkat Ali |
    Tongkat Ali

    The incoming server name stmp.me.com is greyed out in the preference panes and so is the port number??

  • frunny |

    Any new updates on this. I think it is time to send someone at Apple an email. I don't understand why there is no solution to this. Maybe we should mail Steve that it is nice to have a new iPhone4 but an operating Mail.app would be more awesome at this point. I am really angry about this and I invested a ton of hours to get rid of it - reading a lot of webpages and all the solutions seems not to work or only for a few hours until I do a restart of my iMac.

  • Timothy |

    Just received my MBP last week and everything was fine until yesterday when Mail quit working. I can't get emails but I can send them and have tried port 25 and 32 bit mode with no luck. Connection doctor says everything's fine, but obviously it isn't. Don't know if the folks at the Apple store will have any luck, but as it is, I now can only get emails on my iPhone 3GS and my old Mac (non snow leopard), which I'm holding on to until this gets resolved. Still can't figure out why it just stopped? Seems very difficult to troubleshoot and it's nice to know that it's not just me, if that makes anyone feel better. Please Apple, fix this, as I have better things to do.

  • David |

    Thanks for the tips on solving the SMTP problem with Snow Leopard Mail. I had been using the town-provided cable. They provided the Motorola Surfboard modem and I added a Linksys Wireless-G base station. It worked like a charm for me and my wife, who has a Dell laptop running Windows 7.

    Then we upgraded our service to add a couple of VOIP lines. The town took away the Motorola Surfboard and replaced it with an Arris Touchstone modem plus codecs. My wife's Laptop kept on working. I lost the ability to send mail -- until now. I use the custom port 25 setting and authentication set to "none". All is back to normal.

  • gary |

    Nicholas you are a champ! I have 2 providers and not one of them could help me with why I could not send emails. I could send an email to myself but not to anyone else. Update SMTP Authentication section works!!!!

  • Nicholas Mead |
    Nicholas Mead

    Glad it helped Gary :-)

  • Peter Ellis |
    Peter Ellis

    Load Opera for Mac and use the built in email.

  • elgordo |

    Just uninstalled Silverlight and hotmail works like charm

  • Brendan |

    Can not get Mail to work. Has been fine for years but the incoming mail server mail.me.com is greyed. I have been asked for my password a lot recently including when I sync my iPhone.

    Just now when I entered my email with mac.com just below I got a message that it was not a valid email address so I entered my details with me.com and that is fine. I do not want to have to switch to me.com.

    While I have been typing this the mail came in! What is going on. The incoming mail is still greyed.

  • Edsel Colvin |
    Edsel Colvin

    Every time I check my email on MacMail I get the same messages over and over, duplicates and then triplicates, etc. I checked Connection Doctor and it shows two accounts for Frontier. Can I delete one of them without losing everything? I'm an 88 year old dinosaur and I need all the help I can get.

  • Nick Mead |
    Nick Mead

    @Edsel, It does sound like you've got two mail accounts configured and one of them you can probably delete safely. However, to be on the safe side, you should backup what you have by going to "Mailbox Menu>Export Mailbox". Hope this helps.

  • Edsel Colvin |
    Edsel Colvin

    When I go to Mailbox Menu there is no Export Mailbox shown. It has Archive Mailbox but no Export Mailbox. I checked with another MacMail user and his Mailbox Menu shows an Export Mailbox. So, I still don't know what to do but I do appreciate your help.

  • Nick Mead |
    Nick Mead

    @Edsel, If you're still unsure how to backup your Apple Mail, hope this guide helps.

  • Edsel Colvin |
    Edsel Colvin

    Thank you. The guide really helped me. I think I've got it made now!

  • Nick Mead |
    Nick Mead

    @Edsel, Glad it helped! :)

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