Gmail & Mail! Won't send emails.

Discussion in 'Mac Apps and Mac App Store' started by mintos, Jul 20, 2011.

  1. mintos macrumors newbie

    Jul 20, 2011
    Today I added my Gmail account to Mail.

    Mail is not registering any problems when I send from my Gmail account. Anything I send is placed in the 'sent' folder. When I log into Gmail any emails I send (from the Mail app) are present in the Gmail 'sent items' folder. HOWEVER, none of the emails are actually being sent.

    If anybody could help me with my problem it would be greatly appreciated! Let me know if you need any more information. I set it up exactly following these instructions:

  2. saberahul macrumors 68040

    Nov 6, 2008
    Are you on Lion? I am able to send it. Maybe check Google IMAP settings under Gmail settings as it is a good guide that helps in mail set up. Your outgoing server port may be wrong. Problem I am having now is that Mail keeps asking for my password... its annoying.
  3. mintos thread starter macrumors newbie

    Jul 20, 2011
    Thanks for the reply. I just checked again and the ports/servers etc. are correct. I can receive mail but not send it.

    Any emails I try to send ARE present in my gmail (ie. logged in via google) 'sent items' folder, suggesting that Mail must be communicating with the server somehow. Is there anything else I should try?

    ps. Yes I am using Lion.
  4. nickelanddime macrumors member

    Oct 24, 2010
    prepared to get annoyed as hell. youll get a notification bubble for spam, trash, and sent folders
  5. munkery macrumors 68020


    Dec 18, 2006
    Manually enter the password in the settings for the smtp server in the Accounts tab of Mail preferences.
  6. mintos thread starter macrumors newbie

    Jul 20, 2011
    Thanks for the suggestions. It's still not working.

    I have noticed that if I make a label 'Sent messages' in Gmail, then Mail stops displaying the error symbol. Which reads "mail could not locate a Sent Messages folder and has created a local Sent Messages [Gmail] folder instead'. However, I cannot see any such folder and either way messages are not sending.

    I checked again and they are sending fine when I send from

    Has anybody else had a similar problem? It was working before I got Lion.
  7. iammike1 macrumors 6502a


    Oct 25, 2007
    Columbia MD
    First off, you want to turn off the option to save sent messages to server.

    Gmail does this automatically for any emails that are sent through it's SMTP server.

    I recommend looking through this. Click the link then click Apple Mail.
  8. DiegoFrancisco macrumors member

    Jun 10, 2009
    I'm having the same problem; I receive emails but can't send them. Incoming mail server is and the outgoing mail server (SMTP) is

    Anyone know why I can receive but not send messages? I'm baffled. Thanks.
  9. munkery macrumors 68020


    Dec 18, 2006
    In the setting for smtp server, make sure the description is blank, using default port, ssl enabled, password authentication, and password shown masked in text field.
  10. DiegoFrancisco macrumors member

    Jun 10, 2009
    Thanks Munkery, did all of those things but it still won't send mail. It just stays in my outbox:(
  11. DiegoFrancisco macrumors member

    Jun 10, 2009
    Welp, it started working, randomly. Hopefully this continues:) Thanks all
  12. mintos thread starter macrumors newbie

    Jul 20, 2011
    Mine still isn't working. Any other suggestions?

    Also, every email I send from Mail is downloaded twice into Gmail's 'all mail' and 'sent items' folders (organised by Gmail but present/shown in Mail).
  13. munkery macrumors 68020


    Dec 18, 2006
  14. mintos thread starter macrumors newbie

    Jul 20, 2011
  15. Weaselboy Moderator


    Staff Member

    Jan 23, 2005
    Follow Google's interactions in GMail help on how to setup Mail app.

    You need to go to GMail in a browser and in settings tell GMail not to show "All Mail" in IMAP. This will stop the duplicate messages from showing up in Mail app.

    Here and here are the settings you want. Follow these precisely.

    From the Mail menu, click Preferences > Accounts > Mailbox Behaviors
    Store draft messages on the server > do NOT check
    Store sent messages on the server > do NOT check
    Store junk messages on the server > checked
    Delete junk messages when > Never
    Move deleted messages to the Trash mailbox > do NOT check
    Store deleted messages on the server > do NOT check
    If this is your only account in Mail and you have it jacked up, you should just remove the entire account from Mail app and start over. You won't loose any mail.
  16. bangak macrumors member

    May 14, 2010
    I'm having the exact same issue as the OP on my MBP. Here's the strange part though: the same settings are working fine on my iMac.

    I've tried removing the account several times and starting from scratch with no luck. Hardware-specific bug perhaps?

    Oh looks like in Lion will see as much use as it did in Snow Leopard for me.
  17. mintos thread starter macrumors newbie

    Jul 20, 2011
    After playing around for hours and hours it started working! I must have done something right, although I have no idea what. Thanks for all the help!
  18. restricteditaly macrumors newbie

    Mar 31, 2009
    I resolved this exact issue by clicking Mailbox > Rebuild.
  19. AllanW macrumors newbie

    Mar 10, 2015
    Mail won't send messages

    This thread is rather old, but I encountered this problem today and figured out what is doing it on my rig. The posts on this thread seem to have been for Lion, but I am using Yosemite. I think the problem I encountered is the same.

    As others on this thread have, I fumbled around investigating preferences (I hadn't changed them in months!), restarting both Mail and my computer, etc. I had 25 messages in my Outbox and could not move them out. What I finally found and was able to replicate is that some of those messages had addressees which came from Groups in AddressBook. The Groups appeared to expand properly, but didn't really. When I finally looked at the address fields in the unsent messages, the name of the group appeared along with some other characters, which I do not recall. When I replaced the group name with the members of the group from AddressBook, the Outbox opened up and sent everything. My observation is that a message with an improperly formatted group address prevents all further transmission from the Outbox. I had a couple of bad messages among the 25 with the first one being bad. As soon as I fixed that address, it started to send messages until it encountered another bad address and then it stopped.

    I have not been able to figure out how to use groups with the new Mail app, which I think came in just after Snow Leopard. The way groups worked in SL is much more intuitive, but maybe, if I ever figure out how they work in Yosemite, I'll think it's not so bad.

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18 July 20, 2011