Trouble with Yosemite mail?

If you’re having some trouble with Apples latest version of Mail in OS X Yosemite.
You may be in for a fit of anger. I know I was.

Apple in it’s latest attempt to make the OS X Mail Client completely unbearable has decided that it needs to automagically set email settings for you. Except it makes crazy stupid assumptions and keeps resetting *your* manual settings without telling you.

It took me a while to figure this out. But there are 2 easy checkboxes to disable this dumb behaviour and give you back some freedom over what Mail does.

In Mail Preferences, under each account in Advanced there is this little checkbox.
mail1

And in SMTP Server List for each server in Advanced is this similar checkbox.
mail2

Uncheck both. Re-do your settings as you want. Save and restart the client.
Why? Since Apple knows *nothing* about your hosting providers servers it can’t possibly guess the right settings with any accuracy. That’s basic logic. And I wonder what genius (yes!) thought this kind of feature would make sense in any way.

But yes, it’s on by default. And yes it keeps screwing up your settings for no apparent reason.

My main account would try to use a MD5-Challenge response instead of a proper password. And since my servers do not yet use SSL for email and Apple kind of insists on using it it kept enabling SSL for me. How kind. Fuck off!
Geez.

Update: If you do not have the issues described in this post but stuff still isn’t working, check out my other trouble shooting post for some more general tips on email settings, preferred setups and security.

133 thoughts on “Trouble with Yosemite mail?

  1. I have having similar stupid issues with mail. And after wasting half my weekend, I am yet to get this working. A let down.

  2. Hello there!
    Close Mac Mail
    Go and edit /Users/youruser/Library/MailData/accounts.plist

    change Root -> DeliveryAccounts -> 0 -> UserAllowsInsecureAuthentication -> NO to YES.

    All Done!

    Crappy Mail Software…

    Otherwise use ThunderBird.

  3. thank you, thank you and thaaaaank you! that little issue costed me nearly a whole day and many many nerves. but deactivating, deleting my smtp server and re-add it, as suggested, did the trick. thanks again!

  4. Thanks! Was tryign to figure out why I could not get certain email accounts to work and why my manual configuration was being overridden. Yours is the first blog to document it!

  5. Thank you for this fix. I’m moving my primary email to SSL, in order to keep all previous emails in the mail app, I haven’t figured out how to change the incoming mail server on accounts, do you know how this is completed ? I spent DAYS unchecking the damn SSL box until I finally just moved to SSL and now I can’t move the account mail settings for incoming to the new server. This is ridiculous. Please reply if you know how to do this change.

  6. I reported this bug twice since I noticed it on first public beta. Now that I installed the stable version I see they have not fixed it yet. I am very frustrated because none of the solutions written here solved my problem. Tried to uncheck both of checkboxes, removed and added my accounts again, doubled checked everything but it just does not work. I just cannot believe Apple did not pay attention to such a ridiculous bug.

  7. Well, your article did help me to get mail to go out – finally! BUT the danged thing keeps asking for my passwords! Any suggestions on how to make that stop?

  8. Sometimes after changing the settings Mail removes the password. Especially on the SMTP settings. Check your settings again – Fat chance that the password fields are empty. Simply fill them in, save and restart and it should work.

  9. I migrated to Yosemite on my iMac and on my MacBook Pro yesterday, after some time, I couldn’t receive emails on the MacBook Pro for two of my email accounts, while it was still working on the iMac.

    I followed your advice and re-entered the parameters on Mac Book Pro, this has fixed the problem, many thanks for your help that certainly saved me time.

    I don’t know why the issue hasn’t happened on my iMac (yet?), whether the same softaware behaves differently on iMac or whether it depends on other things (e.g. I don’t use the same SMTP on iMac and Mac Book Pro, one has wired connection the other wireless, or something else I haven’t thought about). I left the automatic thing on iMac and will see what happens.

  10. Thank you for at least confirming that Mail for Yosemite is broken.

    1. I’ve restored twice and deleted my primary account in Mail. It does not work in SSL at all and only for receiving mail inconsistently with SSL disabled. Still can’t send email.
    2. The settings do not stick regardless of whether or not I delete the account and start over with a new account in Mail. For example, when I attempt to uncheck the “Automatically detect and maintain account settings”, it rechecks them again along the way.

    They managed to kill the program with no fix at this point. I installed Thunderbird and it worked right out of the box. But it does not integrate with the OS or Daylite (my CRM).

    Mail is the most used program in Apple’s suite. If it doesn’t work, then the ret of their OS becomes almost irrelevant.

  11. If the settings aren’t saved you probably don’t save them when prompted.
    If you do, you may have to delete your mail plist files or other related data in the ~/Library/Mail folder.
    Careful by deleting such files though, it’s invasive, potentially destructive and may disrupt things further if done wrong.

  12. Got the settings to save — finally. The save prompt was not showing so I could save the settings. This happened repeatedly. Still does not work. Now my password is not accepted. Guess I’ll have to contact tech support mail service (Nettica) on Monday. They have not yet been able to help me saying their tests show that I must rest without using SSL. I can receive then, but still can’t send. Gmail account not working consistently either.

  13. Make sure Mail actually stored the password in both IMAP/POP and SMTP settings. Mail has a tendency to remove it when you change settings that invoice security and ports πŸ™‚

    I had to re-enter all passwords and save each account once more after changing my stuff.

  14. Thanks Arnan. This was done… every time I reset up the account from scratch. I can send now, but not receive!!! The problem and inconsistencies continue.

  15. I worked on a system Friday. Regardless of the mail clients Mail, Outlook 2011, and Thunderbird, none will send or receive mail on any pop ports (25,26,110,587). I can use IMAP to see folders, but, anything pop will not work. There are no firewalls enabled, and I set up the account on a mavericks machine with no issues. I also set up a a mail account for a different domain, same issue.

    I’m assuming it could be in a .plist or other settings file that all mail clients use – dunno where to look. The hosts file checks out OK.

    Any suggeations would be greatly appreciated.

  16. If your problem is not specific to Mail (the app) then this post does not necessarily apply to you.
    There are no shared files or plists.

    Either your login details are wrong or there is something else going on, like a firewall, bad router or in the mail server(s) you’re using.

  17. In desperation to read my mail in something other than my browser webmail account, I installed Thunderbird.

    Set up the account settings once and it has worked perfectly for sending and receiving for 3 days.

    Yosemite Mail will either not accept my password or simply refuses to go online. The settings seem to have a mind of their own. Boxes reselect, often it will not allow me to save settings — it’s a broken application.

    Strangely, Gmail works in Mail most of the time. Especially the spam emails.

  18. That’s because Mail is not tied to the user in that sense. So creating a new one won’t make any difference. If your settings are not saving, then that indicates that either you didn’t de-select the options I describe in my post or your mail plist file is corrupt. Removing all Mail data may just solve your problem.

  19. I deleted the mail plist several times.

    Trying it in a new user assures that any plug ins and other software is not causing the problem. It also shows that the user folder is not corrupt. I even tried a full restore to no avail.

    The boxes for automatic settings are also unchecked. I hope my second call to the Nettica email service tech support can help. ☹

    Yosemite as a whole is working well. All Apple and third party software actually performs faster.

    I also deleted the plug ins originally thinking that might be an issue. I also deleted all caches and ktext plist as well as many other possible culprits.

    My wife has the same accounts on her iMac with Mail. Never touched the settings. So I can tell you with a great deal of assurance that it’s a bug(s) in the software.

    We’ll probably see an update of Mail soon.

  20. Thanks for the in formation. Before reading your article I had spent hours trying to send mails and changing lots of settings. Thanks to you I am up and running again but I am unable to syn my mail and calendars with my ISP account (British telecom) but I can live with that.
    Thanks again.

  21. Bless you. I spent several nights this week trying to figure out why my port kept resetting from 25 (suggested by Cox) to 110, 995, 985 or m-o-u-s-e. I never noticed the ‘automagic’ ‘detect email settings’ check boxes. Good on you for finding and posting it.

  22. Haven’t you experience this new on Yosemite Mail bug that when you delete a message in a Intelligent mailbox, it doesn’t disappear, but is left in an estrange state still in the same position in the list, impossible to reread again. It has totally spoiled my daily habit of reading/cleaning my unread messages!

    I’ve filed the bug to

    :((((

  23. The great thing with smart mailboxes is that you can have already sorted your fresh unread email inside their filtered destinations, but then with this smart mb you can read all unread in one mailbox.

  24. Yes, but then the mail is gone from the IMAP server and stored locally, which is not desirable.
    I automatically move my mail around with rules so the IMAP structure stays intact πŸ™‚

  25. I have done above as suggested both and still not working… been tearing my hair out.
    My service provider could not help me either…
    Anyone can help me further?

  26. Well, but smart mailboxes do not change anything in any structure, nor with IMAP nor local, it _only_ displays the unread messages.

  27. Ive installed Yosemite on my early 2008 imac which recently had an SSD drive installed.
    Everything is running as near perfect but since upgrade I have one tiny problem in MAIL – it will not load any images that are part of an html email and instead get little boxes with question marks. Its only minor but I like to have things in order.
    any suggestions?
    Thanks
    C

  28. Many thanks for this post, it helped me solve my issue- I kept getting the following error when setting up Google in System Preferences > Internet Accounts:
    There was a problem setting up the Mail account.
    An unknown error occurred.

    I made the changes and entered my application password in the Mail account information and it worked.

  29. cecil, make sure “Load remote content in messages” is checked in your preferences under the Viewing tab. Also double check your DNS settings your System Preferences -> Network panel. I’ve solved many of these sorts of problems by switching to Google’s DNS servers instead of the ones provided by your ISP. – Thomas

  30. Hi Thomas
    Thanks for the speedy reply. I checked that your first suggestion was done ie β€œLoad remote content in messages” which is was. But I’m a little out of my league when it comes to your second suggestion. I found the network panel but how do I find the Google DNS servers?

  31. It can’t possibly be your DNS if your other internet activities work fine.
    And Google DNS isn’t all that great either – They user your queries for advertising :(.

  32. ok – I will steer clear of Google DNS
    If you do think of any other suggestions please let me know.
    Considering its the only problem Ive encountered with the whole Yosemite install I guess its something I can live with for the time being.
    Thanks again

  33. Cecil, No I don’t have other ideas. If there is no bar at the top of the emails with a button to show images (similar to the brown bar for spam) then perhaps the images can not be loaded because of a permissions issue – You can use “Disk Utility” to repair permissions.

    Never hurts to do that every once in a while.

  34. hi Aran
    For a moment I thought there was an obvious answer that I could kick myself for not thinking of ie: A ‘load images’ button in the tool bar but alas there is not one there even when I look under ‘customise toolbar’
    I’ll let you know how I get on with disc utility
    cheers
    C

  35. Thanks for that tip, it worked! I’d spent 2 hours plus going around in ever decreasing circles. This Mac stuff is alien to me, too many years of MS (which has a variety of decent and easy to set mail clients!

  36. Solved my html image load problem so thought I’d share just in case anyone else encounters the same problem. It struck me out of the blue that I have Little Snitch running in the background, opened the prefs to that app and found a bunch of rules all relating to outgoing connections. No idea how they got there but decided to delete them anyway. Launched Mail, problem solved Happy Man : )

  37. Yes, this issue is a real frustration with Yosemite. Over the course of this week, my Mac Mail chose to not download about 7-10 emails from our 365 server. Thank you–unchecking one box and syncing the Exchange account restored the emails and seems to have fixed the problem instantly–You saved me!

  38. THANKS for the info you posted!
    For some reason it took several attempts to uncheck the boxes in Mail Preferences — I did the uncheck for each email account I have & then clicked SAVE for that account & did the same for the next account, etc. Then I did the SMTP Preferences uncheck for each email account & clicked SAVE for each account.
    FINALLY I can send email from my main accounts again!

  39. Thanks. So much for the computer that just works. Yosemite sux – butt ugly and harder to use in each iteration. I don’t want my Mac to be a big iDevice.

  40. Unfortunately I can’t go back to the last good version of OS X (10.6) because I’m a developer and Apple requires some things like signing Apps for the App store with later versions.

  41. I know little about what happens to make my email work. However, after downloading Yosemite, I shut off my computer and went away for three weeks and used only my iPad and iPhone while I was away. When I got back today I turned on my Mac and no email at all. Your blog was exactly the right answer. Many thanks, The fix was simple and I really appreciate it!

  42. I had a lot of trouble getting my Exchange mailbox to work. It seemed as if it was hanging when trying to set the server configuration.
    What worked for me was to set the account information in offline mode, so that Mail creates the account without checking it, and then go online.

  43. I’ve got the same issue as Juliet. I can receive but not send, even after doing this fix it keeps telling me the SMTP servers are offline.

    I’m on an old 2010 iMac.

    Funny thing is, my 2012 MacBook and all my other devices work fine!

  44. Please remember that when you uncheck the boxes you must then save this setting before it will then allow you to edit the internal and external server areas for an exchange account. If you switch to another e-mail it will ask you if you want to save the settings and you can save them. Then come back and you can now edit the internal and external server boxes. Once you change them to the correct exchange account settings you can then do save them and you are good to go. Thanks, these posts help me to correct my mail account.

  45. I finally got my email to work after several, and I mean several attempts! Now, only part of the file folders came in. How do I get the rest of the folders to come in (in my Inbox)?

  46. On the Apple Support site there is a discussion of this problem:

    https://discussions.apple.com/message/27123227#27123227

    One of the posters says: “More horrible news: Mail looses all of my mail when I change the port that I use to contact to the SMTP server and I have to replace the user->Library->mail folder from a Time Machine backup and and restart Mail to rebuild the mail folders and get it back.”

  47. This is very helpful. What I find most irritating about this is, iCloud email works perfectly well for sending mails, using the automagic settings. So it seems to me as though they are trying to strong arm us away from gmail. Or something.

  48. Hi there , I am new to Mac, I a have changed he settings as well in preferences/advanced but cannot find where to change the SMTP Preferences to complete the 2nd part as advised ?
    Can someone please advise and many thanks ahead

    Kind regards
    Shari

  49. Hi,

    I’ve followed all the instructions on this page but I am still not able to retrieve emails in Mail App on Mac. There is no issue for sending emails.

    I’ve double checked the configuration for incoming and outgoing settings for IMAP.

    The current backup solution is to read emails via Safari at outlook.com.

    Thanks to your help

    Louis

  50. Thank you! You solved my problem. I agree Yosemite is not to the quality you expect from APPLE. I had numerous issues with the upgrade.

  51. Thanks for addressing this. My imap gmail account worked fine for a few weeks, then went wacky. Unchecking that little box has resolved things, at least for now. At least you know that all the time you spent, saved me a bunch of time! Thanks again.

  52. Hi there,
    I have been using Mail for years. Recently it seems that through Facebook some friends are telling me that my ISP is blocking their email. These are people on my contacts list who I have been sending and receiving emails for years. Any advice?
    Thank you!!

  53. ISPs don’t block emails. But if they get some return error or undeliverable reply (via email) that should tell you what’s what.
    For example that your mailbox is over quota or simply they typed the wrong email address or something.

  54. Thank you Arnan. While I consider myself the teeniest of bits, tech savvy, the amount that I don’t understand about my computer and how it works are astounding. Maybe they are using a different email address for me. Glad to have found this resource though.

  55. Has anyone had the problem of deleting emails and then they come back? Since I updated to Yosemite Ive been having this problem.

  56. I used to have three alternate smtp’s. When I tried to solve the “cannot send” problem by checking the “use only this one,” on two of them, they both disappeared. iCloud is listed as “offline,” so won’t send anything, and I don’t know how to get the other two back. Where are they, and how can I do that?

  57. There are plenty of better alternatives then Mail. What? Everything else is better then Mail! What a disastrous email-client is this!!! I really love my Mac… but boy… what do I hate Mail.

  58. Yessssss!!! Thanks a lot for this tip. This fixed a major problem with Apple Mail. There are still others but this one is out of the way. Thanks a lot !!!!

  59. So glad I’m not the only one. Mac Mail is driving me NUTS!

    Endless periods of non-sending, then suddenly it sends again, then more non-sending.

    Also periods where it can’t connect to any of my accounts – and they are all hosted on different servers, so it’s not the mail accounts at fault – and I can get them on my iPhone.

    APPLE, GET YOUR SHIT TOGETHER!

  60. You saved me from the apple hell I’d been living for nearly 6 month, thank you!
    Nearly every day step needed to be saved to the accounts, changing too many settings at once would just ignore what I wanted and turn back on that damn SSL … Finally thanks to your mutual hate, you helped me! πŸ™‚ The folks at MediaTemple had no clue for helping set up the desktop, this did it!

  61. I had a lot of fun with Yosemite mail and this tip (I should have seen that myself) helped a lot. Thanks.
    Two things: Setting up a mail account with SSL is a jungle. Servers can be simple/default level (Yahoo, Gmail) or you might have to call and be walked through by tech help at the server or have proper settings emailed to you. For yosemite always use IMAP- needed for sync to your mobile(s). The ports often require custom settings for an isp.

    At the end of one day, I managed to get email running well, including working pgp and another with a nasty ssl setup on a foreign server for a site I admin.

    .

  62. I do not tend to get fits over things like this, but this time I came close …
    Many thanks for this really helpful tip which finally solved the problems described in this article.

  63. Hi GRA
    My yosemite directory actually is:

    users/youruser/library/mail/v2/maildata/accounts.plist

    and the accounts.plist file doesn’t have that string of words anywhere in it.

  64. I have tried all of your suggestions (very well explained, BTW) and nothing works. I would rather use Apple Mail but until this is fixed have had to switch to Thunderbird. It was a snap to set up 3 email accounts, and is working…..so far.

  65. SMTP Server List for each server in Advanced is this similar checkbox.

    where do I find the SMTP Server List?? thank you.

  66. Thanks for saving my sanity! I can’t tell you how many times I’ve changed the settings (iMac, MacBook Pro, MacAir and three mail accounts) only to later find all changed back after missing an important email or receiving notification “cannot send mail.” Truly the defines insanity with my expatiation of achieving different results after each change. At age 70, I was beginning to wonder . . . Just didn’t take time to read all that was checked, first mistake!

  67. This has been bugging me for ages too. My tedious workaround has been to remove and then re-create the account (once a day sometimes) which is unacceptable. Followed this tip today and hopeful that it will fix it once and for all.
    Thanks.

  68. Hi where do i find the SMTP list.
    I read your comment: “In each account on the general tap, click the dropdown menu for SMTP and click edit SMTP server list.”
    But i have no clue where to find this. Could you be more specific where i can find the dropdown menu?
    Thanks!

  69. @Dagmar: Look in your email preferences under Account Information. Over half way down you see Outgoing Mail Server (SMPT) and you can click on it. Select Edit SMPT Server List; there you can uncheck the box.

  70. Image hyperlinks do not work in Yosemite Apple Mail…
    They work fine in Mavericks and earlier.
    Have you had any experience with this?

  71. I encountered a similar problem and discovered it was Little Snitch running in the background and it had somehow set up a NEW rule not to allow Mail to load images. This solved it for me but obviously this only helps you if you also have Little Snitch.

  72. Thanks Arnan.
    I have tried on multiple computers running Yosemite and Mavericks.
    The image hyperlinks do not work on any emails received on Yosemite’s version of Mail. Text links work fine. I’m wondering if you could email me an image with a hyperlink. I am running 10.10.1 on a mid-2010 MBP and a brand new Mini. Cheers !

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