leopard + mail = driving swissmiss coocoo


Ever since I upgraded to Leopard sending emails has become a real pain in the butt. First I spent hours troubleshooting my keychain issues and now I am trying to get my outgoing servers in Mail to work. I just called my wonderful host mosso and the friendly support fella just chuckled and basically said: “My advice is to download thunderbird and ditch Mail.” (enter sigh here) By the way, I called mosso’s support line and had a real person helping me after it rang twice. I was almost shocked at the speed a real, helpful, friendly person came on. Go Mosso!

Are you having outoing mail server issues with Mail/Leopard as well?

UPDATE 1: Yes, I know, I should move everything to Google/Gmail!

UPDATE 2: Please stop knocking the mosso support guy because of his comment. It was more of a joke and he was VERY helpful and we resolved the outgoing server issue. It might come across as a bad customer support thing to say in my above post but it really wasn’t.

28 Comments leave a comment below

  1. Yep. Everybody I know got the same issues.

    I hate it.

  2. i have yet to move to leopard, but am worried about it a little now. they plan on upgrading my computer at work soon and i get a couple hundred e-mails a day, so it would be great if it was working properly.

    I have gmail and quite honestly I don’t like it. I like the amount of space they give you, but I hate how they display the messages. They display as “conversations” so it’ll have a message you get, then a reply will tack on to the end of it, and if you reply onto the end of that and it keeps on updating a little number on the subject. when i get a new message i want it at the top of the list, as it’s own message so i can see it, like every other e-mail program, I have yet to find a way to make my gmail do this. Yes, i know i can set it up in the mail program, I have done that, but whenever i need a web interface it’s a pain in my ***

  3. This is happening to me too – it’s really annoying.

  4. Mail.app does have a few minor problems. E.g. mine takes ages to evaluate rules on incoming mail. And rules are not applied to mails you have previously read using webmail.

    I however never had any major problem. Specifically not the problem you are describing.

    You might want to post (or email me) the exact error message and any error or warning messages you see in /Applications/Utilities/Console.app at the time the problem occurs.

    You may want to try another SMTP server. Maybe your ISP’s server has troubles with its SMTP server. BTW, it is very easy to run your own SMTP server on your local machine.

    Pierre Bernard
    Houdah Software s.à r.l.
    (author of HoudahSpot and HoudahGeo)

  5. Many people don’t consider Entourage because it’s from Microsoft but forget the Entourage had it’s roots in Emailer which was from Claris. Entourage IMHO has always been much better than Mail especially when dealing with multiple mail accounts. As of last year it was feeling a little crusty (seach felt klunky) but the recent 2008 version brought it back up to par. If you have multiple accounts, use a mix of imap, POP, and exchange services and want your mail downloaded for offline viewing Entourage is well worth a shot.

  6. If you move to Gmail and you’re going to manage multiple email accounts, I can’t recommend the Mailplane app enough. I know it’s not free and you can get Gmail from any browser, but having a dedicated app for Gmail is very handy for me. It depends on your workflow, but Mailplane is constantly improving and very Mac-like.

    Pierre’s suggestion to check with your ISP is good. Many ISPs block outgoing mail ports in an attempt to stop spammers (but in reality spammers aren’t stopped and it just inconveniences the legit users).

    You can use your ISP’s outgoing smtp servers or…

    I’m on Cox and they block port 25, so I had to switch my mail server to listen to port 26. Then in the mail.app program, you have to change your settings.

    Settings > Accounts > Account Information >
    Outgoing Mail Server (SMTP) > Edit Server List (drop-down) > Advanced (tab) > Server port (change to 26)

    Don’t forget to change your server’s SMTP settings to also listen to port 26.


  7. I think the whole process of assigning and testing SMTP servers from Mail.app in Leopard–and in previous versions of Mail–are absolutely broken from a design point of view. When you move around on your laptop, for example, servers that work fine at home, will often not be accessible, so you need to fluidly switch SMTP servers. Good luck. I think the only ‘final’ solution could be a combination of (1) a nicer interface to test the mail server properties separate from the desperate attempt to send a specific email, and (2) tie the SMTP server that we use to given ‘Locations’ which you change from the Apple Menu.

  8. There’s absolutely nothing wrong with Leopard Mail.app. I’ve been using Mail.app for business for years and I’ve never had any major problems. Gmail is fine, but you’re not going to get the responsiveness or customization that you get with a desktop app.

    Regarding your send issues: Do you use AT&T DSL? AT&T used to suggest that all outgoing mail go through their (Yahoo) smtp servers, rather than your ISPs. They recently made changes and I had a hard time getting mail through their servers. As luck would have it, my ISP opens port 587 for smtp traffic, so all I had to do was switch back to using the smtp server recommended by my ISP and change the port to 587 (default is 25). You might want to check to see what your outbound smpt settings are.

  9. Mail.app sucks big time. I have ditched it right away and am using Thunderbird since. Works like a charm, even with Gmail IMAP.

  10. I don’t have any issues with outgoing mail, I use Media Temple. And I think it’s pretty lame that your hosts support suggested moving to a new app. Tina, I think it’s time to move to a new host.

  11. I use Apple Mail with several different accounts. With Gmail (or Google Apps, which I can’t recommend more highly) see this.


    At any rate, it works fine once you pare it down to the outgoing mail servers that work right. There should only be one for each incoming account. And as for Mosso, I use them, but use Google Apps for my email because it just makes more sense. It’s free and their spam blocking and uptime is much better. And if I move my website, don’t have to worry about the mail accounts. Priceless.

    Apple Mail is not perfect, but it’s better than Entourage and it’s better than Thunderbird.

  12. I recently spent some time tearing my hair out providing phone support while my parents set up a new mail account.

    Turns out, when you create a new account, and go to set the outgoing mail server and authentication, Mail tends to append extra junk to the end of the outgoing mail server, but it usually runs out of the input field and you don’t see it.

    My advice is to try creating the account from scratch, and when you set up the outgoing mail authentication, be sure to clear the entire outgoing server field from scratch and then retype it yourself.

    (I apologize for this being vague, since I don’t remember exactly which screen it was) but this absolutely worked and solved my inability to get outgoing mail working.

  13. “be sure to clear the entire outgoing server field from scratch and then retype it yourself”

    Oops, that didn’t make much sense.

    Clear the field entirely, then re-enter the outgoing mail server yourself, rather than relying on the one that auto-populates.

  14. Another vote for Google Apps for Domains, which is gives you GMail but using your domain:

    You get the superb webmail interface, top notch spam filtering, IMAP/POP access which you can then access via Mail.app or other mail client, including remote devices like an iPhone, Blackberry, etc. Oh, and it’s free! (With a paid option for a few additional features and an uptime guarantee.)

    There are a few quirks with using it via IMAP + Mail.app, but as long as you map the “IMAP Path Prefix” and then tell Mail.app to use the respective folders for Trash, Junk and Sent then it works really well.

    I’ve set up several different domains and they’re all functioning perfectly. I’d highly recommend giving it a look.

  15. @Josh

    I used to feel the same way until I forced myself to start using it. Now I can’t live without it.

    I no longer use a local email client, and rely just the online client etc…albeit with addons like better gmail etc

  16. It amazes me how passionate people feel about using gmail and all the google aps. Here are my concerns:

    – I then have to start using Google Contacts and switch everything from my ‘address book’

    – what about being able to write emails offline, when I am in an area without internet connection?

    – what about syncing mail/data with PDA’s?

    Thanks everyone!


  17. Nice to find out that Mosso has such a great approach to support. Instead of resolving the problem with their mail servers they suggest you ditch your software for something that they use. Kind of sounds like a website telling you to use Internet Explorer.

    At least I know I’ll never be using Mosso.

  18. I fourth Google Apps for Your Domain.

    In response to your concerns.

    -Google Contacts – Indeed it is the a weak point. I never really find it to be a problem though, just like Gmail and Mail.app typing in the first few letters of the contacts name, email, business etc, and their address pops right up even if you haven’t saved it in your contacts list.

    -Emails off line – Google Gears (http://gears.google.com/) allows you to run gmail, google docs (also part of the apps for domain suite) as well as other applications off line, saving files locally. Hopefully there will will be a google gears and mozilla prism mash up in the near future.

    -Syncing with PDAs – Gmail has pop and imap access. Gmail is seamless with the iPhone, though of course thats just one phone out of hundreds.

  19. I vote for Apple making Mail.app’s ability to connect to servers generally more robust.

    I’ve had that annoying “offline” lightning bolt showing up about half of the time in recent months. The outgoing mail problem comes up from time to time, too, but not lately.

    These issues are frustrating. You never know what the problem is and no amount of tweaking seems to help. So I just live with it, eventually it goes away, then a couple of months later it starts again.

    Since we’re talking Microsoft, this sort of fussiness isn’t something I’d expect from MS products (even though they’re clunky and ugly).

    In any case, I won’t be switching apps or moving to Gmail. The elegant integration with everything else is worth a bit of annoyance.

  20. Oh yeah… Mail.app has horrible spam filtration, too. I paid for Spam Sieve, an add-on that comes with its own set of problems (not to mention an ugly icon).

  21. Have you tried setting Apple Mail to connect SMTP over Mosso’s SSL (using secure.emailsrvr.com)?

    I’ve had no problems using Apple Mail with Mosso over SSL and you have the advantage of a more secure connection and also avoid all the SMTP problems with ISPs that typically block port 25.

  22. @Tina/swissmiss

    I can’t say I’m passionate about all the other Google App components, just the mail. I use Google Apps/Mail via Apple’s Mail.app (using the IMAP protocol) pretty much exclusively, only reverting to the web interface when I’m travelling without my laptop. Contacts are handled via Address Book, e-mails offline work exactly as with any other Mail.app IMAP account**. It’s all typically Mac-like and generally works the same as any standard IMAP account, outside of a few quirks like the “All messages” and “Flagged” folders.

    ** in Mail’s Preferences, go to the account in question, click the Advanced tab and make sure “Keep copies of messages for offline viewing” is set to “All messages and attachments”. This’ll then make your IMAP mail available through Mail.app when it’s offline.

    As Dusty says, syncing with an iPhone or similar device works fine. (IMAP’s probably a better choice than POP if you’re accessing from multiple devices, e.g. MacBook and iPhone.) See more here:

  23. I use Gmail because I can actually believe the Google engineers are working hard on new solutions everyday

    Inbuilt mail systems don’t seem to be as frequently updated

  24. Have you tried setting Apple Mail to connect SMTP over Mosso’s SSL (using secure.emailsrvr.com)?

    I’ve had no problems using Apple Mail with Mosso over SSL and you have the advantage of a more secure connection and also avoid all the SMTP problems with ISPs that typically block port 25.

  25. Same issue… I find if I keep hitting try again, the 1 click before I get fed-up, it sends. So I solved it by getting fed-up quicker.

    UPDATE: Getting fed-up earlier doesn’t work. ;(

  26. I updated to Leopard without any Mail dramas….and I love the way the Mac mail app blends with my address book contacts and backs itself up automatically with my .mac account, it also tells me when my ichat friends are online with a little green dot beside their names…for me this interconnectivity is the strength of the Mac operating system.

    It would be cool if the outgoing mail server changed automatically when you change your location though, I live between homes in France and London and am always having to switch my smtp server manually.

  27. the best mail is Yahoo mail. Swear to god. It has a drag and drop interface, it updates every 10 minutes so you don’t have to clic the “Receive Button”.

    I use thunderbird at work, it’s old fashionned…

    I use mail at home, besides this sending issue that I also notticed, it is most simple to use and really user friendly…

    And I use yahoo everywhere. It seems like I’ve got a mail client everywhere, it’s really better than mail or thunderbird.
    (got some gmail and hotmail accounts too, but they really suck)

    Gmail is old stuff, really, forget about it. Support Yahoo !

  28. So… “he was VERY helpful and we resolved the outgoing server issue.”

    So why did you do a blog post about this if you were not going to even document the solution? This post is nothing but more words in the static of the internet. Please post your solution so that your blog post may be of some use to someone out there.