Mail 4.5 (1084) won't send

About an hour ago I noticed that the Send icon was twirling constantly.  I have six messages that are stuck in the outbox.  I've tried all the usual tricks short of rebooting -- which I plan to try as soon as I finish this message.  Both on my wife's iMac (Lion) and my MacBook, this is a persistent problem.  We've been running into it for years.  Any advice?  Thanks. - Tony Lima

Actually smaller attachments are downloaded automatically, or perhaps it depends on attachment type? 
Try the same with say 2MB .PPT file .. email the file to yourself. It will come through as "click to download" icon (see image above). Trash the message (before SAVE or clicking on attachment), now try opening it in the trash or pulling it back to inbox and then open it. Attachment is gone and you get garbage - clearly extra data is there but is non-readable.
Not a big issue for a single user - potentially very big issue for an admin supporting large number of end-users, some of which are recent Outlook transplants.
Btw, I'm using IMAP server and I have enabled "Store deleted messages on the server"

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    WROTE Feb 08 08:18:55.309 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba68d5220 -- thread:0x7f9ba68ce300
    CONNECTED Feb 08 08:18:59.021 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
    CONNECTED Feb 08 08:18:59.022 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
    READ Feb 08 08:18:59.066 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
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    READ Feb 08 08:18:59.066 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
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    WROTE Feb 08 08:18:59.085 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
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    WROTE Feb 08 08:18:59.101 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
    EHLO [192.168.0.74]
    READ Feb 08 08:18:59.132 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
    250-mx.google.com at your service, [64.126.140.239]
    250-SIZE 35882577
    250-8BITMIME
    250-STARTTLS
    250 ENHANCEDSTATUSCODES
    WROTE Feb 08 08:18:59.144 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
    STARTTLS
    READ Feb 08 08:18:59.146 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
    250-mx.google.com at your service, [64.126.140.239]
    250-SIZE 35882577
    250-8BITMIME
    250-STARTTLS
    250 ENHANCEDSTATUSCODES
    CONNECTED Feb 08 08:18:59.151 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba6b5ffc0
    CONNECTED Feb 08 08:18:59.154 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba6b45550
    WROTE Feb 08 08:18:59.171 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
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    READ Feb 08 08:18:59.190 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
    220 2.0.0 Ready to start TLS
    READ Feb 08 08:18:59.217 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
    220 2.0.0 Ready to start TLS
    WROTE Feb 08 08:18:59.462 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
    EHLO [192.168.0.74]
    READ Feb 08 08:18:59.508 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
    250-mx.google.com at your service, [64.126.140.239]
    250-SIZE 35882577
    250-8BITMIME
    250-AUTH LOGIN PLAIN XOAUTH
    250 ENHANCEDSTATUSCODES
    READ Feb 08 08:18:59.514 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba6b5ffc0
    * OK Gimap ready for requests from 64.126.140.239 au13if1327927vdc.13
    WROTE Feb 08 08:18:59.528 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
    AUTH PLAIN  (*** 52 bytes hidden ***)
    WROTE Feb 08 08:18:59.541 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba3d925a0
    1.29 CAPABILITY
    READ Feb 08 08:18:59.547 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba6b45550
    * OK Gimap ready for requests from 64.126.140.239 aj13if1332717vdc.2
    WROTE Feb 08 08:18:59.586 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba67202d0
    1.30 CAPABILITY
    READ Feb 08 08:18:59.686 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba3d925a0
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 XYZZY SASL-IR AUTH=XOAUTH
    1.29 OK Thats all she wrote! au13if1327927vdc.13
    READ Feb 08 08:18:59.692 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba67202d0
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 XYZZY SASL-IR AUTH=XOAUTH
    1.30 OK Thats all she wrote! aj13if1332717vdc.2
    WROTE Feb 08 08:18:59.701 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba3d925a0
    2.29 LOGIN (e-mail address edited out) **********
    WROTE Feb 08 08:18:59.715 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba6d41cd0
    2.30 LOGIN  (e-mail address edited out) ********
    WROTE Feb 08 08:18:59.816 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
    EHLO [192.168.0.74]
    READ Feb 08 08:18:59.866 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
    250-mx.google.com at your service, [64.126.140.239]
    250-SIZE 35882577
    250-8BITMIME
    250-AUTH LOGIN PLAIN XOAUTH
    250 ENHANCEDSTATUSCODES
    WROTE Feb 08 08:18:59.885 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
    AUTH PLAIN  (*** 48 bytes hidden ***)
    READ Feb 08 08:18:59.998 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
    235 2.7.0 Accepted
    WROTE Feb 08 08:19:00.016 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
    QUIT
    READ Feb 08 08:19:00.067 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba6d41cd0
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE
    2.30 OK (e-mail address edited out)  (name edited out) authenticated (Success)
    WROTE Feb 08 08:19:00.081 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba7419930
    3.30 CAPABILITY
    READ Feb 08 08:19:00.139 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba3d925a0
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE
    2.29 OK (e-mail address edited out)  (name edited out) authenticated (Success)
    WROTE Feb 08 08:19:00.159 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba6867290
    3.29 CAPABILITY
    READ Feb 08 08:19:00.197 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba7419930
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE
    3.30 OK Success
    WROTE Feb 08 08:19:00.218 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba3d925a0
    4.30 ID ("name" "Mac OS X Mail" "version" "5.1 (1251.1)" "os" "Mac OS X" "os-version" "10.7.2 (11C74)" "vendor" "Apple Inc.")
    READ Feb 08 08:19:00.340 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba3d925a0
    * ID ("name" "GImap" "vendor" "Google, Inc." "support-url" "http://support.google.com/mail" "remote-host" "64.126.140.239")
    4.30 OK Success
    WROTE Feb 08 08:19:00.360 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba3d925a0
    5.30 LIST "" ""
    READ Feb 08 08:19:00.363 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba6867290
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE
    3.29 OK Success
    WROTE Feb 08 08:19:00.387 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba7419930
    4.29 ID ("name" "Mac OS X Mail" "version" "5.1 (1251.1)" "os" "Mac OS X" "os-version" "10.7.2 (11C74)" "vendor" "Apple Inc.")
    READ Feb 08 08:19:00.474 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba3d925a0
    * LIST (\Noselect) "/" "/"
    5.30 OK Success
    WROTE Feb 08 08:19:00.496 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba67202d0
    6.30 LOGOUT
    READ Feb 08 08:19:00.606 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
    235 2.7.0 Accepted
    READ Feb 08 08:19:00.623 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba7419930
    * ID ("name" "GImap" "vendor" "Google, Inc." "support-url" "http://support.google.com/mail" "remote-host" "64.126.140.239")
    4.29 OK Success
    WROTE Feb 08 08:19:00.626 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
    QUIT
    WROTE Feb 08 08:19:00.643 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba7419930
    5.29 LIST "" ""
    READ Feb 08 08:19:00.847 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba7419930
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    5.29 OK Success
    WROTE Feb 08 08:19:00.869 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba7419930
    6.29 LOGOUT

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  • I'm using ipad2 with ios5. My outbox won't send mail. I guess i need an outgoing server and can't find it anywhere.

    I'm using ipad2 with ios5. My outbox won't send mail. I guess i need an outgoing server and can't find it anywhere. Any suggestions on how to get it to send. I have tried everything, rebooting, ensuring passwords are correct, etc.

    My problem is i don't have an outgoing server spot on my menu.  These are my selections. After getting to the menu that where i enter my password for hotmail, i have the following menu choices:  Email, then server (bay-m.hotmail.com, then domain (empty), then username, then password, thendescription, then Use SSL, then S/MIME
    I don't see or can find an outgoing server choice. My daughter has an ipad2 using Ios4 and she has all the choices that are illustrated on. All the help sites. I only have the ones listed above.

  • Outbox won't send mail

    Had a problem earlier with my email account (Yahoo) being hacked, After resetting password all seemed to be well, but now my iPad won't send mail, it goes into OUTBOX but won't send. Receiving mail is no problem.
    I am new to iPad and need a bit of help.
    Thanks
    John

    Brilliant! Thanks Jaimi E.
    My iPad did resume 'normal service' after an overnight rest. I did not know that there was an imposed 24hr quarantine, but I do know that all's well now.
    I found The BT staff in their technical help desk were good at fixing the original hacking problem on my laptop, but totally helpless at sorting the iPad issues out.
    I had to talk to Apple help desk in UK who in turn put me through to the USA. Their consultant was great, but he undoubtedly didn't seem to aware of the quarantine imposed by Yahoo. I will try to get this information through to him for future information
    Thanks to all for your assistance.
    My message to anyone who reads this topic and has been hacked on Yahoo (or btinternet) is
    1 update security passwords on laptop. New password required. Delete all traces of hacked messages (inc failed delivery notices and real people's responses)
    2 uninstall your mail settings on iPad and reinstall with new mail password on iPad.
    3 the iPad mail system should then receive, but not send mail (goes into Outbox)
    4 wait 24 hours then everything will be back to normal.
    As a brand new user and about to go on a long holiday, it was a nightmare, but ended up fine!
    Now in Singapore at 6am local time, can't sleep so catching up on my machine which functions perfectly!

  • Mail replies won't send in OS 10.8.3

    Replies to mail messages that have a link within the message won't "send" unless I delete the link and any other messages beneath the message I am replying to .  Message hangs up in activity window . I've checked with my ISP and all is fine there.  My older iMac running OS 10.6.8 mail works flawlessly .  What is going on here?  New messages "send" o.k.   So I'm clueless and bummed about what appears to be some mail glitch on ML.
    Also, what is this new "envelope shaped" mail format with the blue border ?  Is there some option to change the format back to the regular " letter shaped" mail format ?
    Thanks for any help !
    Carolyn.  a.k.a. gladys2

    So far, no big change, but I have figured out how to circumvent the problem by just deleting anything  I'm replying to other than the last message in a group of "back and forth" mail.  (if that makes any sense).  Its a minor hassle, but I'm not willing to risk messing up things by getting into areas where I'm not comfortable.... like messing with the Library.
    I did run Repair Permissions a couple of times after I had tried everything else that was obvious, shut down, unplugged and restarted. I also sent an e-mail to Apple support and told them what I thought about Mail in ML.
    It comforts me somewhat to see that there are a lot of folks out there with the same type problems, each with variations on the theme ! :-)
    I do appreciate all you suggested.  If you come up with any other easy ideas, let me know.  You are a good guy to show concern and try to help !
    Carolyn

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