#651 new
Patrick

Problem connecting to gmail over SSL in os x 10.9.2

Reported by Patrick | February 25th, 2014 @ 09:10 PM

After the recent update security(ssl handling), the connection fails to get mail.

Clearing connection to imap.gmail.com
Clearing connection to imap.gmail.com
Trying to connect to imap.gmail.com on port 993
Successful connection on socket 11.
Initiating secure connection...
Error: Failed SSL handshake.
Clearing connection to imap.gmail.com
Trying to connect to imap.gmail.com on port 143
Error: Time limit (15s) reached while trying to write data (imap.gmail.com)
Error: Failed while trying to connect to “imap.gmail.com” on socket 11.
Clearing connection to imap.gmail.com
Clearing connection to imap.gmail.com
Trying to connect to imap.gmail.com on port 993
Successful connection on socket 11.
Initiating secure connection...
Error: Failed SSL handshake.
Clearing connection to imap.gmail.com
Trying to connect to imap.gmail.com on port 143
Error: Time limit (30s) reached while trying to write data (imap.gmail.com)
Error: Failed while trying to connect to “imap.gmail.com” on socket 11.
Clearing connection to imap.gmail.com
Clearing connection to imap.gmail.com
Trying to connect to imap.gmail.com on port 993
Successful connection on socket 11.
Initiating secure connection...
Error: Failed SSL handshake.
Clearing connection to imap.gmail.com
Trying to connect to imap.gmail.com on port 143
Error: Time limit (60s) reached while trying to write data (imap.gmail.com)
Error: Failed while trying to connect to “imap.gmail.com” on socket 11.
Clearing connection to imap.gmail.com
Clearing connection to imap.gmail.com
Trying to connect to imap.gmail.com on port 993
Successful connection on socket 11.
Initiating secure connection...
Error: Failed SSL handshake.
Clearing connection to imap.gmail.com
Trying to connect to imap.gmail.com on port 143
Error: Failed connecting to host (imap.gmail.com:143).
    “error:0200203C:system library:connect:Operation timed out”
    “error:2007306E:BIO routines:CONN_STATE:nbio connect error”

Comments and changes to this ticket

  • benny

    benny February 26th, 2014 @ 10:03 AM

    Does this problem persist? I don't seem to have any problems connecting my Gmail accounts?

    Are you on a slow network?

    You can hardcode the settings to use port 993 since Gmail does not support port 143 (although that is the recommended IMAP port). That'll focus MailMate on retrying on port 993.

  • Patrick

    Patrick February 26th, 2014 @ 08:35 PM

    yes, it happened again today a few times now. The internet connection that I have is rock solid. I'll try the hard coded port and see if that helps. Having the email go offline for a while and not show me the new stuff is pretty frustrating.

  • benny

    benny February 27th, 2014 @ 08:12 PM

    I fully understand the frustration. I'll do what I can to help.

    You wouldn't happen to be located in Dallas? I have another user who had a weird problem cause by a Verizon issue described here.

  • Patrick

    Patrick February 27th, 2014 @ 08:23 PM

    I appreciate it Benny... I am actually in Southern California and not on Verizon.

  • benny

    benny February 27th, 2014 @ 09:47 PM

    When this happens then what is the result of running the following in the Terminal:

    openssl s_client -crlf -connect imap.gmail.com:993
    

    Just to make sure that it's only MailMate which cannot connect.

  • Patrick

    Patrick March 1st, 2014 @ 05:39 PM

    The result is that the command line invocation worked correctly. "Gimap ready for commands"

    The account is stuck in a failed state with the activity indicator just spinning.

    Error: Failed SSL handshake.
    Clearing connection to imap.gmail.com
    Synchronizing mailbox (attempting to do it quickly): Deleted Messages
    Selecting mailbox: Deleted Messages
    Clearing connection to imap.gmail.com
    Trying to connect to imap.gmail.com on port 993
    Successful connection on socket 11.
    Initiating secure connection...
    Setup of secure connection complete (TLSv1).
     Cipher: RC4-SHA                 SSLv3 Kx=RSA      Au=RSA  Enc=RC4(128)  Mac=SHA1
    

    The rest of the activity monitor pretends that it's synchronizing but it doesn't actually do it for the inbox as I know that there are a few emails that are not showing up like they should(checked via iphone mail)

  • Patrick

    Patrick March 2nd, 2014 @ 08:18 PM

    So it happened again and the activity viewer was open during the wind up to it... a bunch of ssl handshake errors. I did the openssl command that you wanted and it seemed to work fine:

    ~ ❯❯❯ openssl s_client -crlf -connect imap.gmail.com:993
    CONNECTED(00000003)
    depth=2 /C=US/O=GeoTrust Inc./CN=GeoTrust Global CA
    verify error:num=20:unable to get local issuer certificate
    verify return:0
    ---
    Certificate chain
     0 s:/C=US/ST=California/L=Mountain View/O=Google Inc/CN=imap.gmail.com
       i:/C=US/O=Google Inc/CN=Google Internet Authority G2
     1 s:/C=US/O=Google Inc/CN=Google Internet Authority G2
       i:/C=US/O=GeoTrust Inc./CN=GeoTrust Global CA
     2 s:/C=US/O=GeoTrust Inc./CN=GeoTrust Global CA
       i:/C=US/O=Equifax/OU=Equifax Secure Certificate Authority
    ---
    Server certificate
    -----BEGIN CERTIFICATE-----
    MIIEdjCCA16gAwIBAgIINAwAQ8mvPHwwDQYJKoZIhvcNAQEFBQAwSTELMAkGA1UE
    <snip>
    UWSWdpnGsCUUEq+/ys7IH6tWYtt1CcRuA9v88W8li/668+RZDXIDWWR3
    -----END CERTIFICATE-----
    subject=/C=US/ST=California/L=Mountain View/O=Google Inc/CN=imap.gmail.com
    issuer=/C=US/O=Google Inc/CN=Google Internet Authority G2
    ---
    No client certificate CA names sent
    ---
    SSL handshake has read 3238 bytes and written 444 bytes
    ---
    New, TLSv1/SSLv3, Cipher is RC4-SHA
    Server public key is 2048 bit
    Secure Renegotiation IS supported
    Compression: NONE
    Expansion: NONE
    SSL-Session:
        Protocol  : TLSv1
        Cipher    : RC4-SHA
        Session-ID: 71F46B1A43A53F29CE5476FDCE31A7C981303AF4A997AB080369806D5F803385
        Session-ID-ctx:
        Master-Key: A58A6EDFE4B4FFC937F0C0379AE745BDA6A10ACE9C09D9127BAAB8EA83D0F774662F48A13F67037305866EE267E713F9
        Key-Arg   : None
        Start Time: 1393791125
        Timeout   : 300 (sec)
        Verify return code: 0 (ok)
    ---
    * OK Gimap ready for requests from redacted r3mb74853211oav
    
  • benny

    benny March 3rd, 2014 @ 09:03 AM

    Thanks for the openssl output. It's a tricky problem since I cannot reproduce it (I have a couple of Gmail accounts online).

    When this happens does it then always work when you restart MailMate?

    If you get another log in Activity Viewer leading up to this then you are very welcome to share it. I might spot something non-obvious (or get an idea of what I could add to find out more about the problem).

  • Patrick

    Patrick March 5th, 2014 @ 07:04 PM

    I attached some of the output I am seeing when the accounts go offline. Hopefully this gives you something to go on.

  • benny

    benny March 10th, 2014 @ 01:32 PM

    Hold down ⌥ when clicking “Check Now” to fetch the latest test version. I've tried changing some things and adding a bit more debug output. As before, keep the Activity Viewer open and provide the final lines of the logs as you did before.

    Thanks in advance!

  • Patrick

    Patrick March 10th, 2014 @ 09:24 PM

    here are some logs from the beta version. It hasn't gone to unavailable yet but the failed handshakes are present with some more information if it might help.

  • benny

    benny March 11th, 2014 @ 09:19 AM

    @Patrick: Thanks, this output looks as expected. It doesn't explain why the SSL handshakes fail, but for now I'll assume this is a server issue and threat it as gracefully as possible. Note to myself: I really should add some time stamps to those logs :-)

  • Patrick

    Patrick March 11th, 2014 @ 08:45 PM

    here is one from when the account actually is unavailable.

  • Stuart Ashdown

    Stuart Ashdown March 11th, 2014 @ 11:29 PM

    Hi Benny

    Thanks for the reply in the other thread - I'm pretty sure it's the same issue. Here is an extract of my log. BTW - I really like this software - nice work.

    S: D25 OK Success
    Disconnecting
    Trying to disconnect nicely...
    C: R26 LOGOUT
    S: * BYE LOGOUT Requested
    S: R26 OK 73 good day (Success)
    Clearing connection to imap.gmail.com
    Synchronizing mailbox (attempting to do it quickly): Follow up
    Selecting mailbox: Follow up
    Clearing connection to imap.gmail.com
    Trying to connect to imap.gmail.com on port 993
    Successful connection on socket 34.
    Initiating secure connection...
    Error: Failed SSL handshake.
    Error code: (9)

    And then it continues to have issues with the SSL handshake

  • benny

    benny March 12th, 2014 @ 09:27 AM

    @Stuart: So for you it never clears up, but if you restart MailMate then it works again?

  • Stuart Ashdown

    Stuart Ashdown March 12th, 2014 @ 11:21 AM

    It will only get better if:
    1. I take the account offline and then online again, or
    2. I restart mailmate

  • Stuart Ashdown

    Stuart Ashdown March 13th, 2014 @ 08:20 PM

    Hi Benny

    Here is an extract of the log from version 4069

    Clearing connection to imap.gmail.com
    Clearing connection to imap.gmail.com
    Trying to connect to imap.gmail.com on port 993
    Successful connection on socket 18.
    Initiating secure connection...
    Error: Failed SSL handshake (0).
    Error code: (9)

    Error: Failed multiple retries (4). Final error code was 9.

  • benny

    benny March 17th, 2014 @ 02:04 PM

    Sorry about the late reply. Once again, I suggest fetching the latest test version. I haven't really looked into this particular problem, but the SSL handshake might include a more verbose error message now. Also, I've done some work on IMAP timeout values although I doubt this has any effect on this issue.

    Thanks for the feedback!

  • Stuart Ashdown

    Stuart Ashdown March 18th, 2014 @ 01:44 AM

    Thanks Benny

    Here is the end of the more verbose log:

    Clearing connection to imap.gmail.com
    Clearing connection to imap.gmail.com
    Trying to connect to imap.gmail.com on port 993
    Successful connection on socket 49.
    Initiating secure connection...
    Error: Failed SSL handshake (4294967295).
    Error code: (9)

    Error: Failed multiple retries (4). Final error code was 9.

  • benny

    benny March 18th, 2014 @ 12:58 PM

    Yet another test version in a few minutes. I still have no idea what the problem is. I did fix a (presumably) unrelated problem.

    Enable some additional (chaotic) output like this:

    defaults write com.freron.MailMate MmDebugSSLHandshake -bool YES
    

    Maybe it'll provide the hint I need to make progress on this issue.

  • Patrick

    Patrick March 18th, 2014 @ 09:17 PM

    benny,

    I haven't really had the error as frequently as before but maybe this will help:

    C: D16 NOOP
    S: D16 OK Success
    Performing full synchronization.
    S: D17 OK Success
    S: D18 OK Success
    S: D19 OK Success
    Disconnecting
    Trying to disconnect nicely...
    C: R20 LOGOUT
    S: * BYE LOGOUT Requested
    S: R20 OK 73 good day (Success)
    Clearing connection to imap.gmail.com
    Synchronizing mailbox (attempting to do it quickly): [Gmail]/Archive
    Selecting mailbox: [Gmail]/Archive
    Clearing connection to imap.gmail.com
    Trying to connect to imap.gmail.com on port 993
    Successful connection on socket 74.
    Initiating secure connection...
    BIO_do_handshake failed: Cause is: 2, BIO_FLAGS_WRITE
     bio1: 0x2078a990, bio2: 0x236ccad0
     looping
    BIO_do_handshake failed: Cause is: 0, unknown
     bio1: 0x2078a990, bio2: 0x2078a990
    Error: Failed SSL handshake (0/0).
    Error code: 9
    Clearing connection to imap.gmail.com
    Synchronizing mailbox (attempting to do it quickly): [Gmail]/Archive
    Selecting mailbox: [Gmail]/Archive
    Clearing connection to imap.gmail.com
    Trying to connect to imap.gmail.com on port 993
    Successful connection on socket 74.
    Initiating secure connection...
    BIO_do_handshake failed: Cause is: 2, BIO_FLAGS_WRITE
     bio1: 0x2331fe50, bio2: 0x20787d30
     looping
    BIO_do_handshake failed: Cause is: 2, BIO_FLAGS_WRITE
     bio1: 0x2331fe50, bio2: 0x20787d30
     looping
    Setup of secure connection complete (TLSv1).
     Cipher: RC4-SHA                 SSLv3 Kx=RSA      Au=RSA  Enc=RC4(128)  Mac=SHA1
    
  • Stuart Ashdown

    Stuart Ashdown March 19th, 2014 @ 12:16 PM

    Hi Benny

    Please see attached extract of the log - thanks again for your continued help.

  • benny

    benny March 19th, 2014 @ 12:40 PM

    Thanks to both of you. Based on the output, I think it's pretty clear that you are having the same issue. As far as I can see the output from Patrick shows that the connection succeeds when retried, but the first error is identical to the repeated error in the output from Stuart.

    I'm running out of ideas and it's hard to debug when I cannot reproduce the issue myself, but I appreciate your patience.

    One quick attempt is to ignore the error reported and keep retrying for 15 seconds. This is done with this test version when MmDebugSSLHandshake is enabled. I don't really think it'll work, but it's worth a shot.

  • benny

    benny March 19th, 2014 @ 01:31 PM

    Here is another test version to try, but I would still like to know if the previous one made any difference.

    For this one you should enable this debug variable:

    defaults write com.freron.MailMate MmSkipSSLHandshake -bool YES
    

    (It doesn't really mean that the handshake is skipped. It means that it is postponed until it is needed.)

    Thanks in advance.

  • Stuart Ashdown

    Stuart Ashdown March 20th, 2014 @ 05:46 AM

    Fingers crossed but it has behaved itself all day today!

  • benny

    benny March 20th, 2014 @ 01:06 PM

    @Stuart: Is this with or without the MmSkipSSLHandshake?

    (Unfortunately, I don't really like the MmSkipSSLHandshake fix since it doesn't really tell me anything about what the problem is.)

  • benny

    benny March 21st, 2014 @ 10:00 AM

    Another test version is available. I would like you to try out these settings:

    defaults write com.freron.MailMate MmSkipSSLHandshake -bool NO
    defaults write com.freron.MailMate MmUseDirectSSLHandshake -bool YES
    

    As noted I don't like MmSkipSSLHandshake and I seem to have problems when waking my machine from sleep (I don't know for sure that this is a related issue). With MmUseDirectSSLHandshake I'm using a slightly different API to make the handshake.

    Sorry about all the test versions, but it's necessary as long as I cannot reproduce the issue myself.

  • Stuart Ashdown

    Stuart Ashdown March 24th, 2014 @ 05:18 AM

    Hi Benny

    Sorry, but I ditched google and am now using polarismail. All works very well thanks - hence I purchased the product. Thanks for your great support, sorry I couldn't be of more assistance.

  • Christoph Kania

    Christoph Kania April 28th, 2014 @ 02:55 PM

    I had the same problem and I guess that it came up with the last Mac OS update I installed yesterday (security update 2014-002).
    Now it works with the latest beta 1.7.2 (4199) after reboot.

  • Erno Kaikkonen

    Erno Kaikkonen May 31st, 2014 @ 04:36 AM

    I've had the same problem with 3905. I'm upgrading to 4229 to see if that fixes the issue.

  • benny

    benny June 8th, 2014 @ 06:20 PM

    @Erno: Did it fix the issue?

  • John N

    John N July 10th, 2014 @ 12:27 PM

    I had this problem for some time, and it seems to be fixed by installing the latest beta and changing the settings for SkipSSLHandshake and DirectSSLHandshake (I didn't try it after installing the newest version and before changing the settings). Thanks!

  • benny

    benny July 10th, 2014 @ 12:42 PM

    • State changed from “new” to “fixcommitted”

    @John: Thanks for the feedback. I've changed the default behavior and I suspect it would have worked without changing the settings. I'll change the ticket state.

  • benny

    benny October 15th, 2014 @ 03:32 PM

    • State changed from “fixcommitted” to “fixreleased”
  • Des Dougan

    Des Dougan December 21st, 2014 @ 07:21 AM

    Benny,

    I hit this issue tonight on an Exchange server I support (I've MailMate configured to use IMAP and it has worked OK till now on my infrequent sends from this server). I was testing email for my client, who'd reported an issue with sending. I tried a test that wouldn’t go out. I was able to send OK from my iPhone (ActiveSync) and through Outlook Web Access. I searched for the error and found this thread.

    I ran the openssl command you'd suggested (see below). Rather than open a new thread, I decided to add to this one - I hope that's OK. I'm running Version 1.8 (5029) (64-bit).

    If there's anything further I can do that would help, please let me know.

    openssl s_client -crlf -connect mail.****.com:993
    CONNECTED(00000003)
    depth=0 /CN=mail.****.com
    verify error:num=20:unable to get local issuer certificate
    verify return:1
    depth=0 /CN=mail.****.com
    verify error:num=27:certificate not trusted
    verify return:1
    depth=0 /CN=mail.****.com
    verify error:num=21:unable to verify the first certificate

    verify return:1

    Certificate chain
    0 s:/CN=mail.****.com

    i:/CN=BIIG-HP-SERVER-CA

    Server certificate
    -----BEGIN CERTIFICATE----- MIIFMDCCBBigAwIBAgIKHPtqAwAAAAAABzANBgkqhkiG9w0BAQUFADAcMRowGAYD
    VQQDExFCSUlHLUhQLVNFUlZFUi1DQTAeFw0xNDAyMTIyMzQ3MDlaFw0xNjAyMTIy
    MzQ3MDlaMCExHzAdBgNVBAMTFm1haWwuYmlpZ2ZpbmFuY2lhbC5jb20wggEiMA0G
    CSqGSIb3DQEBAQUAA4IBDwAwggEKAoIBAQCuPCmxgKA+NO1fFg34l56ydJorP/BP
    u6/BXKcE2dql0SyHrXJW7dIiZfH/R5TD1C7+dbGZpZasNXXf1DyXv6zideKBhUSm
    W1PrVhtSK6DKY9Gb8+6coBZRhEjg3quSIbKOzoCdB9TTqusOl1WT76hUhe+D0dmE
    P/tuDFLZieNry5fXJAVyryBzA83ZliIsDYEv3Y+IhGLFns5q7K60ly8CWfjFRYHn
    bXfLNaMMjtYfBTITMp4j+qbPCF7/lE5KMfLnm/A3saHXfHqbFJy2ByBwyClDUIyX
    FnEAKTfjRSlf5GgjB33Bh7YY+u3Cj9BFmmefrlCggzkY+3Qo5KjLTlodAgMBAAGj
    ggJtMIICaTAdBgNVHQ4EFgQUrmIR5YQd9dEApXeKzxCPMSooClUwCwYDVR0PBAQD
    AgWgMEoGA1UdEQRDMEGCEWJpaWdmaW5hbmNpYWwuY29tghZtYWlsLmJpaWdmaW5h
    bmNpYWwuY29tghRIUC1TRVJWRVIuQklJRy5sb2NhbDAfBgNVHSMEGDAWgBR+ssaO
    FncuhOnwg/OlxZ8z5dQmSjCB0AYDVR0fBIHIMIHFMIHCoIG/oIG8hoG5bGRhcDov
    Ly9DTj1CSUlHLUhQLVNFUlZFUi1DQSxDTj1IUC1TRVJWRVIsQ049Q0RQLENOPVB1
    YmxpYyUyMEtleSUyMFNlcnZpY2VzLENOPVNlcnZpY2VzLENOPUNvbmZpZ3VyYXRp
    b24sREM9QklJRyxEQz1sb2NhbD9jZXJ0aWZpY2F0ZVJldm9jYXRpb25MaXN0P2Jh
    c2U/b2JqZWN0Q2xhc3M9Y1JMRGlzdHJpYnV0aW9uUG9pbnQwgcIGCCsGAQUFBwEB
    BIG1MIGyMIGvBggrBgEFBQcwAoaBomxkYXA6Ly8vQ049QklJRy1IUC1TRVJWRVIt
    Q0EsQ049QUlBLENOPVB1YmxpYyUyMEtleSUyMFNlcnZpY2VzLENOPVNlcnZpY2Vz
    LENOPUNvbmZpZ3VyYXRpb24sREM9QklJRyxEQz1sb2NhbD9jQUNlcnRpZmljYXRl
    P2Jhc2U/b2JqZWN0Q2xhc3M9Y2VydGlmaWNhdGlvbkF1dGhvcml0eTAhBgkrBgEE
    AYI3FAIEFB4SAFcAZQBiAFMAZQByAHYAZQByMBMGA1UdJQQMMAoGCCsGAQUFBwMB
    MA0GCSqGSIb3DQEBBQUAA4IBAQDIoTE1QuAiE5YNVHEFlZ+57NMFqA6knnd6pqna
    AZyXNA+PGu+Wkq4i5XF/OIo45niQ9Es1UPgvWgQJysEbrFFgnBKv+d1OmwBU7ups
    waL9z0hGSt2HYGSxoeRjSudYPifZ6ylZLumlZAXZbZ0Rg16NeTWkSgvRzUs54ZF3
    wC4U2cvQQCnCSIVAE183um7QOGM2dwh1SlzksEHnv0fOoYR8XN1PD7HAi6/vE2g1
    xY+ulWQS2SPSOr9hrBdByUvfKmSqRHchREdm1XKJN3+vTSgp6RkGj+UJblw+00uQ
    YR3aTPB4NVPhAjadU7fK2xO63jZhhxsUMtm8R9gQDS+blJgp
    -----END CERTIFICATE----- subject=/CN=mail.****.com

    issuer=/CN=BIIG-HP-SERVER-CA

    No client certificate CA names sent

    SSL handshake has read 1491 bytes and written 456 bytes

    New, TLSv1/SSLv3, Cipher is AES128-SHA
    Server public key is 2048 bit
    Secure Renegotiation IS supported
    Compression: NONE
    Expansion: NONE
    SSL-Session:
    Protocol : TLSv1 Cipher : AES128-SHA Session-ID: DA2C000094D61E89F2CE16D21BEF1E83FA2EDE35BFE3D63A35E3048E862D89CE Session-ID-ctx: Master-Key: 3B047901F35DA6B60595F74552611F289DBD80DD4C41C349E119132C73EF3A0A2521F6091C523D6A65EBEA33E7EA87F8 Key-Arg : None Start Time: 1419133463 Timeout : 300 (sec)

    Verify return code: 21 (unable to verify the first certificate)

    • OK The Microsoft Exchange IMAP4 service is ready.
  • benny

    benny December 21st, 2014 @ 09:48 AM

    So you can connect via openssl, but MailMate cannot connect to the server? Do you have some output/error from MailMate as well?

  • Des Dougan

    Des Dougan December 21st, 2014 @ 07:07 PM

    The send error dialog shows:

    Failed connecting to host (mail.****.com:465).
        “error:0200203C:system library:connect:Operation timed out”
        “error:2007306E:BIO routines:CONN_STATE:nbio connect error”
    

    I opened Activity Viewer and captured this:

    19:00:10 Running action
    19:00:10 Sending request (3450)
    19:00:10 Handling request
    19:00:10 Ready to run action
    19:00:10 Clearing connection to mail.****.com
    19:00:10 Trying to connect to mail.****.com on port 993
    19:00:10 Successful connection on socket 103.
    19:00:10 Initiating secure connection...
    19:00:11 Setup of secure connection complete (TLSv1).
    19:00:11  Cipher: AES128-SHA              SSLv3 Kx=RSA      Au=RSA  Enc=AES(128)  Mac=SHA1
    19:00:11 S: * OK The Microsoft Exchange IMAP4 service is ready.
    19:00:11 C: A0 CAPABILITY
    19:00:11 S: * CAPABILITY IMAP4 IMAP4rev1 AUTH=NTLM AUTH=GSSAPI AUTH=PLAIN UIDPLUS CHILDREN IDLE NAMESPACE LITERAL+
    19:00:11 S: A0 OK CAPABILITY completed.
    19:00:11 Retrieving password (keychain or user request)
    19:00:11 C: A1 AUTHENTICATE PLAIN
    19:00:11 S: +
    19:00:11 C: ••••••••••
    19:00:11 S: A1 OK AUTHENTICATE completed.
    19:00:11 C: A2 CAPABILITY
    ...
    19:00:12 Completed action (1003). Observed read/write timeouts: 8/8
    
    19:00:12 Handling reply
    

    Thanks,

    Des

  • benny

    benny December 21st, 2014 @ 07:50 PM

    The log is from IMAP (port 993), but the reported problem is for SMTP on port 465. Port 465 is non-standard and not all servers behave the same on this port. MailMate currently has a problem with that, but you can force MailMate to work (I believe) by entering 465s instead of just 465 in the settings window.

  • Des Dougan

    Des Dougan December 21st, 2014 @ 08:37 PM

    Same error using 465s.

    Activity log shows:

    20:30:00 Sending request (480)
    20:30:00 Handling request
    20:30:00 Clearing connection to mail.****.com
    20:30:00 Ready to run action
    20:30:00 Clearing connection to mail.****.com
    20:30:00 Trying to connect to mail.****.com on port 465s
    20:30:12 Error: Failed connecting to host (mail.****.com:465s).
        “error:0200203C:system library:connect:Operation timed out”
        “error:2007306E:BIO routines:CONN_STATE:nbio connect error”
    20:30:12 Error code: 2
    20:30:12 Failed action (0). Reset observed read/write timeouts: 18/18
    
    20:30:12 Handling reply
    

    I have captured 465 and 587 (which gives a relay error instead of the one seen on 465/465s, although SSL is selected):

    20:32:33 Sending request (971)
    20:32:33 Handling request
    20:32:33 Clearing connection to mail.****.com
    20:32:33 Ready to run action
    20:32:33 Clearing connection to mail.****.com
    20:32:33 Trying to connect to mail.****.com on port 465
    20:32:46 Error: Failed connecting to host (mail.****.com:465).
        “error:0200203C:system library:connect:Operation timed out”
        “error:2007306E:BIO routines:CONN_STATE:nbio connect error”
    20:32:46 Error code: 2
    20:32:46 Failed action (0). Reset observed read/write timeouts: 18/18
    
    20:32:46 Handling reply
    20:33:09 Sending request (992)
    20:33:09 Handling request
    20:33:09 Clearing connection to mail.****.com
    20:33:09 Ready to run action
    20:33:09 Clearing connection to mail.****.com
    20:33:09 Trying to connect to mail.****.com on port 587
    20:33:09 Successful connection on socket 39.
    20:33:10 S: 220 mail.****.com Microsoft ESMTP MAIL Service ready at Sun, 21 Dec 2014 12:33:09 -0800
    20:33:10 C: EHLO [192.168.150.89]
    20:33:10 S: 250-mail.****.com Hello [184.70.128.202]
    20:33:10 S: 250-SIZE 10485760
    20:33:10 S: 250-PIPELINING
    20:33:10 S: 250-DSN
    20:33:10 S: 250-ENHANCEDSTATUSCODES
    20:33:10 S: 250-STARTTLS
    20:33:10 S: 250-AUTH
    20:33:10 S: 250-8BITMIME
    20:33:10 S: 250-BINARYMIME
    20:33:10 S: 250 CHUNKING
    20:33:10 C: STARTTLS
    20:33:10 S: 220 2.0.0 SMTP server ready
    20:33:10 Initiating secure connection...
    20:33:10 Setup of secure connection complete (TLSv1).
    20:33:10  Cipher: AES128-SHA              SSLv3 Kx=RSA      Au=RSA  Enc=AES(128)  Mac=SHA1
    20:33:10 C: EHLO [192.168.150.89]
    20:33:10 S: 250-mail.****.com Hello [184.70.128.202]
    20:33:10 S: 250-SIZE 10485760
    20:33:10 S: 250-PIPELINING
    20:33:10 S: 250-DSN
    20:33:10 S: 250-ENHANCEDSTATUSCODES
    20:33:10 S: 250-AUTH
    20:33:10 S: 250-8BITMIME
    20:33:10 S: 250-BINARYMIME
    20:33:10 S: 250 CHUNKING
    20:33:10 C: MAIL FROM:<des@****.com> SIZE=705
    20:33:10 S: 250 2.1.0 Sender OK
    20:33:10 C: RCPT TO:<des@****.com>
    20:33:16 S: 550 5.7.1 Unable to relay
    20:33:16 Error: Unexpected return code 550 (expected 250):
    “5.7.1 Unable to relay”.
    20:33:16 Error: The following recipients were rejected by the SMTP server:
        des@****.com
    
    
    Unexpected return code 550 (expected 250):
    “5.7.1 Unable to relay”.
    20:33:16 Error code: 1
    20:33:16 Failed action (0). Reset observed read/write timeouts: 18/18
    
    20:33:16 Handling reply
    20:33:46 Sending request (993)
    20:33:46 Handling request
    20:33:46 C: QUIT
    20:33:46 S: 221 2.0.0 Service closing transmission channel
    20:33:46 Clearing connection to mail.****.com
    20:33:46 Ready to run action
    20:33:46 Clearing connection to mail.****.com
    20:33:46 Completed action (3). Observed read/write timeouts: 18/18
    
    20:33:46 Handling reply
    
  • benny

    benny December 21st, 2014 @ 08:45 PM

    Ok, 587 is much better. You should use that, but I don't know why the server is rejecting the email address. That seems to be a server issue and not a MailMate issue?

  • Des Dougan

    Des Dougan December 22nd, 2014 @ 12:34 AM

    Thanks, Benny. I checked the settings on the server and it's now working OK using 587.

    Is it possible to mask the domain name in this thread?

  • benny

    benny December 22nd, 2014 @ 09:32 AM

    @Des: I've updated your comments to exclude domains/addresses.

  • Des Dougan

    Des Dougan December 22nd, 2014 @ 02:24 PM

    Benny,

    Many thanks.

    Des

Please Sign in or create a free account to add a new ticket.

With your very own profile, you can contribute to projects, track your activity, watch tickets, receive and update tickets through your email and much more.

New-ticket Create new ticket

Create your profile

Help contribute to this project by taking a few moments to create your personal profile. Create your profile »

Mac OS X email client.

Shared Ticket Bins

People watching this ticket

Attachments

Referenced by

Pages