.Mail won't send attachments
Since upgrading to OS X 10.7, Mail usually won't send attachments. It does not matter if the attachment is small (~300kb) or larger (~3MB). Mail will try to send it (and if you watch the progress bar in the lower right corner of Mail, you can see that it starts uploading the message), but then it stops. Then I get the message: "Cannot send message using the server..." Occsaionally, attachments will work, but I haven't been able to determine why. This is the case for both my desktop (10.7.2) and my laptop (10.7.3).
The e-mail affected is a g-mail account configured through IMAP. I have verified that I have internet connectivity while experiencing this problem and I can even send other e-mails w/o file attachments. I opened the Connection Doctor and everything logs in/out correctly. The details from Connection Doctor are below.
Any ideas?
Thanks.
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
220 mx.google.com ESMTP li19sm4211728pbb.17
READ Feb 08 08:18:59.066 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
220 mx.google.com ESMTP a5sm2518813pbh.15
WROTE Feb 08 08:18:59.085 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
EHLO [192.168.0.74]
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
STARTTLS
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
* LIST (\Noselect) "/" "/"
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
I am going to try removing the account from mail and then setting it up again to see if it solves the issue.
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