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outlook 2016 vpn RRS feed

  • Question

  • ###getting flagged has spam####

    issue:  Outlook not generating packets to outlook.office365.com when vpn is connected.  outlook has to be started first before establishing a vpn connection which holds the established connection to outlook.office365.com.  The search function does not work on vpn because it requires a new outlook.office365.com tcp connection.

    Firewall/antivirus disabled.  wins7 64bit.   cisco asa configured for split tunneling.  wins 7 routing table with vpn adapter active is valid and optimal.  I have troubleshooted with wireshark and tcpview.  No packets are escaping to vpn tunnel destined for outlook servers.  No other programs are having problems.

    ogs using tcpview, not sending packets to authenticate to outlook.office365.com.


    NON VPN (Outlook runs perfectly off the VPN)

    OUTLOOK.EXE 7276 TCP 56726 a88-221-189-148.deploy.akamaitechnologies.com https ESTABLISHED 3 812 6 7,384

    OUTLOOK.EXE 7276 TCP 56728 login.microsoftonline.com https ESTABLISHED 5 2,335 12 11,376

    OUTLOOK.EXE 7276 TCP 56729 login.microsoftonline.com https ESTABLISHED 2 376 5 3,849

    OUTLOOK.EXE 7276 TCP 56730 login.microsoftonline.com https ESTABLISHED 3 2,045 7 6,382

    OUTLOOK.EXE 7276 TCP 56731 a69-192-69-99.deploy.akamaitechnologies.com https ESTABLISHED 4 1,396 6 5,659

    OUTLOOK.EXE 7276 TCP 56732 outlook.office365.com https ESTABLISHED 14 8,491 789 301,633

    OUTLOOK.EXE 7276 TCP 56733 52.109.88.5 https ESTABLISHED 3 726 3 4,933

    OUTLOOK.EXE 7276 TCP 56736 outlook.office365.com https ESTABLISHED 18 9,967 17 14,678

    OUTLOOK.EXE 7276 TCP 56741 outlook.office365.com https ESTABLISHED 32 18,821 32 27,948

    OUTLOOK.EXE 7276 TCP 56750 191.233.95.85 https ESTABLISHED 3 2,787 3 5,369

    OUTLOOK.EXE 7276 TCP 56751 191.233.95.85 https ESTABLISHED 3 2,787 3 5,369

    OUTLOOK.EXE 7276 TCP 56752 191.233.95.85 https ESTABLISHED 3 2,771 3 5,369

    OUTLOOK.EXE 7276 TCP 56753 outlook.office365.com https ESTABLISHED 54 41,187 57 45,071

    OUTLOOK.EXE 7276 TCP 56754 outlook.office365.com https ESTABLISHED 8 4,605 18 9,963

    OUTLOOK.EXE 7276 TCP 56755 outlook.office365.com https ESTABLISHED 24 15,378 29 25,219

    OUTLOOK.EXE 7276 TCP 56756 40.115.1.44 https ESTABLISHED 4 6,583 9 6,226

    OUTLOOK.EXE 7276 TCP 56757 40.115.1.44 https ESTABLISHED 4 14,567 8 6,125

    OUTLOOK.EXE 7276 TCP 56760 outlook.office365.com https ESTABLISHED 4 1,673 4 5,605

    VPN (Will only authenticate if connection is already made off VPN)

    OUTLOOK.EXE 9140 TCP 56888 ip-184-168-221-47.ip.secureserver.net http SYN_SENT

    OUTLOOK.EXE 9140 TCP 56890 login.microsoftonline.com https ESTABLISHED 2 376 5 3,849

    OUTLOOK.EXE 9140 TCP 56891 login.microsoftonline.com https ESTABLISHED 3 2,045 7 6,382

    OUTLOOK.EXE 9140 TCP 56892 login.microsoftonline.com https ESTABLISHED 3 821 10 7,867

    OUTLOOK.EXE 9140 TCP 56910 40.115.1.44 https ESTABLISHED 3 12,464 2 576

    OUTLOOK.EXE 9140 TCP 56911 40.115.1.44 https ESTABLISHED 2 6,170 3 677


    Search function also establishes a new connection with outlook.office365.com, explaining why it doesn't work in conjunction with the program opening up when VPN is established.

    Wins event logs
    When application starts with VPN on
    Warning 03/02/2018 16:12:24 Outlook 58 None
    During launch an existing non-responsive instance of Outlook was closed.
    When using search on vpn
    Warning 03/02/2018 16:36:39 Search 10023 Gatherer
    The protocol host process 2452 did not respond and is being forcibly terminated {filter host process 9732}.

    Would really appreciate any input in going forward with this issue.

    Saturday, February 3, 2018 9:57 PM

Answers

All replies

  • This happens for new forums users that have not yet been verified. You can expedite verification by replying to this thread with your request.


    Regards, Dave Patrick ....
    Microsoft Certified Professional
    Microsoft MVP [Windows Server] Datacenter Management

    Disclaimer: This posting is provided "AS IS" with no warranties or guarantees, and confers no rights.



    Saturday, February 3, 2018 10:33 PM
    Moderator
  • Strange. Sam's profile shows he asked a question 3 times in the Outlook IT Pro forum, and all are deleted. We cannot tell who deleted the posts. Did Sam? Still, Sam's account needs to be verified, as it is new.

    Richard Mueller - MVP Enterprise Mobility (Identity and Access)

    Sunday, February 4, 2018 12:19 AM
    Moderator
  • Strange. Sam's profile shows he asked a question 3 times in the Outlook IT Pro forum, and all are deleted. We cannot tell who deleted the posts. Did Sam? Still, Sam's account needs to be verified, as it is new.

    Guessing spam filter but I asked fissues an hour or so ago but no reply yet.

      edit: update. 

    Turns out all three deleted by user. Sam just post again and ignore the spam message. The thread is not marked spam, the message you're getting is misleading. This happens for new forums users that have not yet been verified. 

     

     



    Regards, Dave Patrick ....
    Microsoft Certified Professional
    Microsoft MVP [Windows Server] Datacenter Management

    Disclaimer: This posting is provided "AS IS" with no warranties or guarantees, and confers no rights.





    Sunday, February 4, 2018 12:20 AM
    Moderator