Blog Post

Mangled Mail? That’ll Be the New Cat

Mail icon

Ooops. Seems I spoke too soon. TidBITS reports that some users who upgraded to Snow Leopard, Apple’s (s aapl) latest incarnation of its Mac OS X operating system, have been experiencing problems sending email using the native email client,

When trying to send mail, hapless users have been getting an error message that reads “Error 54: Connection Reset By Peer.”

Of course, I know what you’re thinking. “Error 54?” you’re saying, as you stroke your Tech Guy Beard of Truth, “Sounds like an issue with port rotation. I probably need to update my SMTP settings.”

A quick look at the newly added Article TS2998 over on Apple’s Support Knowledge Base confirms your Oracle-like insight. According to Apple:

In Mac OS X v10.6, Mail sends messages through a different port rotation for the “Default ports” setting. Your authentication settings for your Mail account (for outgoing messages) may need to be updated.

Just follow step-by-step instructions for updating the offending account’s SMTP server settings.

Several days ago, during Gmail’s recent hiccup, I had just upgraded my machines to Snow Leopard and found I couldn’t send mail from my Gmail account. At the time, I assumed it was caused by the server difficulties Google (s goog) was having and, seeking a quick and easy fix, I removed the account from Mail and have been using Safari to check my Gmail ever since. It seems, perhaps, I was wrong to assume it was Google’s problem. Perhaps I was experiencing exactly the problem described above.

I don’t feel too foolish for failing to suspect my new big cat was the culprit; after all, everything else works perfectly. Following such a major upgrade, all my hardware and software work exactly as they did on the old feline. I’d like to extend the metaphor a little further — probably something about cats toying with their prey — but I’m gonna stop before it gets outta hand.

Have you experienced the same problem with Mail? Did the fix Apple recommend work for you? Is this a bug in Snow Leopard, or the result of Mail becoming a more secure email client? Share your thoughts with me in the comments, and I promise I won’t use the cat metaphor again.

23 Responses to “Mangled Mail? That’ll Be the New Cat”

  1. I have cable internet access via Comcast and upon upgrading to Snow Leopard Mail stopped working. I previously used port 110. I could receive mail but not send. Talked to Apple support who suggested I change to port 587 and now I can send mail but not receive. I have Entourage (2004) on my computer and it does work. I prefer Mail for most things, but have not successfully worked the issue out. If anyone has any ideas I’d be obliged.

  2. Mail has decided to periodically refuse to send or store as a draft on the basis that some attachments are too large. Yesterday it did this to a message I had already sent and was sending to someone else .This happens on my Mac Pro and my mac book.

    The same messages handle fine on gmail

  3. Mail is working fine for me with MobileMe set up … however, getting really frustrated with Address Book integration, specifically not being able to click a group to add to the ‘To’ or ‘CC’ field.

  4. I maintain five iMacs and I have to agree, it is a reliable and solid app with a clean UI. My own Mac has over 30,000 emails in the Completed box, downloads from MobileMe and two other mail servers, and I have nearly zero problems.

    After installing Snow Leopard, one of our computers appeared to quad-duplicate emails, and apparently this is a known bug. As far as I can tell, no one has died from this and Apple appears unlikely get out of the software business.

    • Kimberly J.

      Did I really read that right?? The new Mail App QUADRUPLICATED ALL 30,000 of your emails??!! Man, I’ll bet that was a pain in the backside to fix! I don’t think I could even fathom having to go through and delete that many duplicate emails!!

  5. i cant get mail to work at all…. talked to apple and they had no clue, there are tons of websites with mail crashing and it appears there arent clear solutions, man how frustrating

  6. Didn’t notice a thing… except for how simple it was to add an Exchange 2007 account to Mail (which btw already ran with a GMail account).

    Very fast search, and great connection to Exchange… I don’t miss Outlook that’s for sure :))

    Oh and this is valid for both my iMac and (unibody) Macbook that I upgraded to Snow Leopard on Day 1.

    • Kimberly J.

      What is “Exchange 2007”? I don’t think I am familiar w/ that one. I’ve heard of MS Entourage but I don’t think I’ve heard of that one. Is that another one of MS’s desparately lame attempts at creating a decent STABLE mail client?

    • Kimberly J.

      Am I assuming that by “predator MS”, you are referring that GIGANTIC MONOPOLY OF A COMPANY … MICROSOFT??

      When did those two companies get “married” (so to speak)?? I don’t remember hearing anything in the news about that!!

      Kim J.

  7. John Dingler

    Apple’s Email has never worked for me, neither in OS9, nor in OSX Leopard, even consulting with online help sites. I have given up on Email. I feel like the Lone Ranger since you all managed to get it working at some point. I really want to use it.

    So I use either .gmail or .mail, and sometimes yahoo. Disappointed with Email.

  8. @ McRat & Hagen Kaye:

    As someone who supports Apple’s Mail app on over 200 computers daily, I can tell you that you don’t know what you’re talking about.

    Perhaps you have had problems, (I wouldn’t deny that there are never problems), but overall Mail is as rock solid as you can get for email clients. Rarely have I ever seen anyone have a problem with it once the account was set up, whereas with Eudora, Outlook or any other client you care to name there are often very frequent “hiccups” and sometimes even crashes.

    Why not make it clear when you post that “in your experience” or “for you” there have been problems with Mail, instead of making it seem like the program is buggy for everyone, when you obviously don’t even know if it is?

    You’ve already got “Veit” believing you (above) and putting up an ad for his favourite client, when in fact Mail is an excellent program. It’s probably a better choice for the average user than Thunderbird due to it’s simplicity (even though Thunderbird is a good choice for many also), but regardless, I can tell you from experience that it’s certainly far better than most clients out there.

    • Gazoobee, you couldn’t be more right! I support over 750 end-users…A WIDE range of clients including Thunderbird, Apple Mail, Outlook, Outlook Express, Eudora and every mobile device you can think of (Blackberry, iPhone, Pocket PC, Palm Treo, etc). As the go-to-guy to make this stuff work I highly agree with you. Thunderbird is a solid client, however, for the end-user experience I have found Apple Mail.App to be a far more friendly experience with the interface with the stability Thunderbird offers.

      I know I have had multiple users that have had connectivity issues with Thunderbird when going from one version (1.x to 2.x) to another using the original config file and having it read that in incorrectly at application loading, causing the need to refresh…even more impactful than what is required to resolve this particular Apple Mail issue.

      No mail client is perfect (don’t I wish one were!) But, if you have to support people using a tool I’d take Apple Mail over anything else as my app of choice due to the fact I view it as “Best of Breed”. Now, if we could only get Apple to port the App to Windows!

  9. I’d have to agree, every version of Mail on every version of OS X has had connection problems once in awhile or the darn forgetting the password dialog pops up. Or cant’ send email, but if you send a second email it can and will send the first. I don’t expect to ever improve.

    I’d nearly given up squawking about it, well at least until now, had to squawk one more time.

  10. Osmodious

    Yup…oddly enough, only ONE of my three email providers is a problem, and it’s the one for my ISP. Go figure. That is not the exact error that I get, though, I just get the ‘could not use this server, pick another one’ dialog box. So, I go in and change my username and password, and it seems to work. It’s a bit weird…

  11. Every rev of Apple Mail has had strange connectivity problems.

    While many people have never seen problems, enough people HAVE had enough problems that it doesn’t seem very reliable.