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Time Warner blocks gmail imap via Outlook

The gmail webmail service is fantastic and provides most of my needs. However, imap can keep everything in sync from what I understand and with that being the case, there are still email cleanup tasks that would be easier in Outlook as would importing old mail from some prior PST files.

I finally bit the bullet today and started to try and figure out how to connect gmail to Outlook 2013. Apparently there are some restrictions.

According to this guide http://darktips.com/set-up-gmail-in-outlook-2013/#comment-846 the only thing other than default that is required is the imap port 993, with ssl encryption and tlp encryption for the default smtp port 25.

I get this error http://screencast.com/t/z1BCtE3Ooq.

Assistance in finding a way through this is greatly appreciated.

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David Johnson, CD

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ASKER

Thanks for all the help. I am now trying it from a DSL connection and still no luck. Here is a video http://screencast.com/t/uoqQfF3gxJNX illustrating the errors I got

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David Johnson, CD

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ASKER

Did the uncheck and tried everything else also. Still nothing. Here is the error screenshot http://screencast.com/t/PgKOFKyTO

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David Johnson, CD

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ASKER

Arnold, yes. Why do you ask?

Incomming imap.gmail.com 993 ssl requires login and password
Outgoing smtp.gmail.com 586 tls does not require login and password

I've put this in correctly again today and still can't resolve it.

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ASKER

Hi Arnold. Here is a video of what I did with Putty, not sure if I have it right http://screencast.com/t/pkkpamM8V.

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ASKER

Thank you sir for your reply and for helping us figure this out. I'm having some trouble following your train of thought with respect to using Open SSL to begin with. Here is a video of my most recent attempt http://screencast.com/t/C0qkl7gAlQO.

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David Johnson, CD

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ASKER

Thank you for the video. That helped me run the command. I got slightly different output though. Still confused.

Microsoft Windows [Version 6.2.9200]
(c) 2012 Microsoft Corporation. All rights reserved.

C:\Users\Ted>openssl s_client -connect imap.gmail.com:993
'openssl' is not recognized as an internal or external command,
operable program or batch file.

C:\Users\Ted>cd c:\

c:\>openssl s_client -connect imap.gmail.com:993
'openssl' is not recognized as an internal or external command,
operable program or batch file.

c:\>cd windows

c:\Windows>openssl s_client -connect imap.gmail.com:993
'openssl' is not recognized as an internal or external command,
operable program or batch file.

c:\Windows>cd ..

c:\>dir
 Volume in drive C has no label.
 Volume Serial Number is F03E-F1D6

 Directory of c:\

07/31/2013  10:43 PM                 0 END
11/07/2007  08:00 AM            17,734 eula.1028.txt
11/07/2007  08:00 AM            17,734 eula.1031.txt
11/07/2007  08:00 AM            10,134 eula.1033.txt
11/07/2007  08:00 AM            17,734 eula.1036.txt
11/07/2007  08:00 AM            17,734 eula.1040.txt
11/07/2007  08:00 AM               118 eula.1041.txt
11/07/2007  08:00 AM            17,734 eula.1042.txt
11/07/2007  08:00 AM            17,734 eula.2052.txt
11/07/2007  08:00 AM            17,734 eula.3082.txt
11/07/2007  08:00 AM             1,110 globdata.ini
11/07/2007  08:44 AM           855,040 install.exe
11/07/2007  08:00 AM               843 install.ini
11/07/2007  08:44 AM            75,280 install.res.1028.dll
11/07/2007  08:44 AM            95,248 install.res.1031.dll
11/07/2007  08:44 AM            90,128 install.res.1033.dll
11/07/2007  08:44 AM            96,272 install.res.1036.dll
11/07/2007  08:44 AM            94,224 install.res.1040.dll
11/07/2007  08:44 AM            80,400 install.res.1041.dll
11/07/2007  08:44 AM            78,864 install.res.1042.dll
11/07/2007  08:44 AM            74,768 install.res.2052.dll
11/07/2007  08:44 AM            95,248 install.res.3082.dll
07/21/2013  11:53 PM    <DIR>          Intel
08/02/2013  02:44 PM    <DIR>          OpenSSL-Win32
07/26/2012  02:33 AM    <DIR>          PerfLogs
08/01/2013  06:32 PM    <DIR>          Program Files
08/01/2013  08:34 PM    <DIR>          Program Files (x86)
07/21/2013  11:41 PM    <DIR>          Users
11/07/2007  08:00 AM             5,686 vcredist.bmp
11/07/2007  08:50 AM         1,927,956 VC_RED.cab
11/07/2007  08:53 AM           242,176 VC_RED.MSI
07/29/2013  10:51 PM    <DIR>          Windows
              25 File(s)      3,947,633 bytes
               7 Dir(s)  394,843,758,592 bytes free

c:\>cd Openssl-win32

c:\OpenSSL-Win32>openssl s_client -connect imap.gmail.com:993
'openssl' is not recognized as an internal or external command,
operable program or batch file.

c:\OpenSSL-Win32>dir *.exe
 Volume in drive C has no label.
 Volume Serial Number is F03E-F1D6

 Directory of c:\OpenSSL-Win32

08/02/2013  02:44 PM           715,038 unins000.exe
               1 File(s)        715,038 bytes
               0 Dir(s)  394,843,684,864 bytes free

c:\OpenSSL-Win32>dir *.exe/s
 Volume in drive C has no label.
 Volume Serial Number is F03E-F1D6

 Directory of c:\OpenSSL-Win32

08/02/2013  02:44 PM           715,038 unins000.exe
               1 File(s)        715,038 bytes

 Directory of c:\OpenSSL-Win32\bin

02/11/2013  09:36 AM           393,728 openssl.exe
               1 File(s)        393,728 bytes

     Total Files Listed:
               2 File(s)      1,108,766 bytes
               0 Dir(s)  394,843,684,864 bytes free

c:\OpenSSL-Win32>openssl s_client -connect imap.gmail.com:993
'openssl' is not recognized as an internal or external command,
operable program or batch file.

c:\OpenSSL-Win32>cd bin

c:\OpenSSL-Win32\bin>openssl s_client -connect imap.gmail.com:993
WARNING: can't open config file: /usr/local/ssl/openssl.cnf
Loading 'screen' into random state - done
CONNECTED(00000180)
depth=1 OU = generated by avast! antivirus for SSL scanning, O = avast! Mail Sca
nner, CN = avast! Mail Scanner Root
verify error:num=19:self signed certificate in certificate chain
verify return:0
---
Certificate chain
 0 s:/C=US/ST=California/L=Mountain View/O=Google Inc/CN=imap.gmail.com
   i:/OU=generated by avast! antivirus for SSL scanning/O=avast! Mail Scanner/CN
=avast! Mail Scanner Root
 1 s:/OU=generated by avast! antivirus for SSL scanning/O=avast! Mail Scanner/CN
=avast! Mail Scanner Root
   i:/OU=generated by avast! antivirus for SSL scanning/O=avast! Mail Scanner/CN
=avast! Mail Scanner Root
---
Server certificate
-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----
subject=/C=US/ST=California/L=Mountain View/O=Google Inc/CN=imap.gmail.com
issuer=/OU=generated by avast! antivirus for SSL scanning/O=avast! Mail Scanner/
CN=avast! Mail Scanner Root
---
No client certificate CA names sent
---
SSL handshake has read 2330 bytes and written 639 bytes
---
New, TLSv1/SSLv3, Cipher is AES256-GCM-SHA384
Server public key is 2048 bit
Secure Renegotiation IS supported
Compression: NONE
Expansion: NONE
SSL-Session:
    Protocol  : TLSv1.2
    Cipher    : AES256-GCM-SHA384
    Session-ID: 22B58896BE8A06E41B6586F2BFDD7B5901B4E90E87208268FCA90005DD8CE96A

    Session-ID-ctx:
    Master-Key: B365E5063559047ABBE564E80F92EC0967CF65EF640B7687D0A6F90F40BA4C74
AA95BD0AA646081842D0AE953AB74CB3
    Key-Arg   : None
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    TLS session ticket lifetime hint: 300 (seconds)
    TLS session ticket:
    0000 - 40 fd d1 b6 d2 51 d5 7e-98 b3 3b ae 3b 13 92 d0   @....Q.~..;.;...
    0010 - a2 52 06 ec 10 a8 7e 57-df 04 13 0f 59 35 08 80   .R....~W....Y5..
    0020 - d0 5b a7 6e a6 75 3f ff-ec a3 cd 79 55 ee f2 94   .[.n.u?....yU...
    0030 - 89 c2 b8 f1 56 e3 7c 8c-3a 57 e9 c7 1b b8 d1 0a   ....V.|.:W......
    0040 - d3 33 15 e7 54 6a ff 5a-cf 26 12 f6 a0 48 3a 54   .3..Tj.Z.&...H:T
    0050 - 39 ac ba 2d 25 5f 48 03-c0 e0 b0 2b 42 0a 5b d5   9..-%_H....+B.[.
    0060 - 7d ab eb 93 7f ab eb d6-1c f7 70 82 37 68 d8 b7   }.........p.7h..
    0070 - 41 09 7d 09 33 53 d4 d7-00 c0 3d dd 60 96 95 e5   A.}.3S....=.`...
    0080 - ed 6f 25 6a 17 87 52 7e-2a cd f6 33 2c 72 7b 75   .o%j..R~*..3,r{u
    0090 - f4 71 41 b2 0d c2 ce 18-59 0d 22 ae 22 9b 8f 2a   .qA.....Y."."..*

    Start Time: 1375495639
    Timeout   : 300 (sec)
    Verify return code: 19 (self signed certificate in certificate chain)
---
* OK Gimap ready for requests from 72.178.132.192 f3if5342893oay.91

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SOLUTION

David Johnson, CD

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ASKER

Wow, I must have said yes to every authorization but it FINALLY WORKED! I need to save the shortened version of these steps so that they aren't so painful the next time. THANK YOU for the walk-through. You gave me the energy to try a 10th time.

There was something called PAP Authorization that I missed. I'm trying to put the settings in the smallest possible space.

imap.gmail.com require ssl 993, may have been an 'authentication checkbox' here?
smtp.gmail.com require tls and ssl 465, yes to two 'require authentication' checkboxes - purpose unclear
global 'require authentication' checkbox - purpose unclear

Assistance in making this clearer and easier for next time would be greatly appreciated.

ASKER CERTIFIED SOLUTION

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