Cisco Anyconnect Outlook Disconnected

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Symptoms

  • Outlook 2010 Cisco anyconnect latest version (split tunnel) Websense endpoint client for proxy. When working remotely, if I boot up my laptop connect to WiFi and start outlook, outlook connects via Outlook anywhere just fine. But if I close Outlook and connect to vpn, reopen Outlook it fails to connect to thr exchange server.
  • Apple: Wifi gets disconnected when connecting to VPN via Cisco AnyConnect ClientHelpful? Please support me on Patreon: https://www.patreon.com/roelvandepaar.

When you have the Cisco AnyConnect Secure Mobility Client installed on a Surface Pro 3, you may experience one of the following symptoms:

My Cisco Anyconnect VPN Client keeps on disconnecting after I changed my laptop and upgraded to windows 10. My internet connection is same and it was working fine on my previous laptop. In Device Manager under Network Adapter I see a warning sign on my Microsoft Wi-Fi Direct Virtual Adapter. Re: Outlook/Office 365 is not working when turning VPN on. How do the client IP addresses compare to the exchange server's IP address. If the clients and exchange server are both in Denmark and you are doing a client VPN full tunnel to Sweden then it locks you out of anything not on the same subnet and can lock you out of anything local at all. Jan 31, 2017 I have observed this issue is when there is a manual proxy set on the browser & user connected to VPN either Cisco or Sonicwall. If you remove the proxy all works fine & as expected. This is an issue with Windows 7 32 & 64 bit only. With settings Windows 10 works fine. Any clue why Outlook 2013/2016 behaves differently in both the cases.

  • If you try to connect to a wireless network by using the Cisco Network Access Manager (NAM), you cannot connect to the wireless network.

  • You can connect to an open (that is, unsecured) wireless network by using the Cisco Network Access Manager (NAM). However, you cannot use the Cisco NAM to connect to a wireless network that requires a password or other authentication.

  • If you use the Windows 8.1 Networks interface to connect to the wireless network, you can connect to the wireless network.

Cisco Anyconnect Outlook Disconnected Version


TL;DR If Cisco AnyConnect is disconnecting, reconnecting every few minutes, try blocking UDP in/out ports for the vpnagent executable/service.
Cisco AnyConnect Secure Mobility Client version 4.7.04056
This one drove me nuts for the longest time until I found time to dedicate to troubleshooting it myself. Symptoms were that my AnyConnect client had been disconnecting, reconnecting every few minutes (2:50 to be exact!), which would, in turn, timeout my RDP session. Total reconnect time was only a few seconds, but you can imagine how having your concentration broken every three minutes is a productivity killer!Anyconnect
I had troubleshot this with my ISP, Comcast/Xfinity and my customer (whose site I was connecting to via VPN). Both essentially were pointing fingers at each other. It would be easy to blame the ISP because the problem didn't happen over my hotspot, but I can't help but think that the VPN server wasn't configured to properly handle such situations. Anyway, I decided to live with it (for far too long) until I could do some troubleshooting myself and figure out next steps.

Cisco Anyconnect 4.9 Outlook Disconnected

My troubleshooting steps are below, in case anyone is interested.

Cisco Anyconnect Outlook Disconnected Email


Microsoft Outlook Disconnected

Wireshark

Wireshark VPN test-2019-12-09-A.pcapng

Wireshark VPN test-2019-12-09-G-Comcast.pcapng

Wireshark VPN test-2019-12-09-F-Hotspot.pcapng

Wireshark VPN test-2019-12-09-E-Comcast-Reconnect at 129 sec.pcapng

Wireshark VPN test-2019-12-09-D-Hotspot.pcapng

Wireshark VPN test-2019-12-09-C-Comcast-Reconnect at 91 sec.pcapng

Wireshark VPN test-2019-12-09-B.pcapng

Noticed that most application traffic happens via DTLS (OpenSSL) over UDP, but every 20 seconds, there's a TLSv1.2 transmission from the client [PSH, ACK], but no response from the server.Client retransmits the [PSH, ACK] in intervals of 0.3, 0.6, 1.2, 2.4, 4.8, 9.6 seconds, and then sends a RST.

Google search

cisco vpn client tls every 20 seconds no ack

Article above references this, which was the most helpful

As long as DTLS is enabled, the client applies the DTLS MTU (in this case 1418) on the VPN adapter (which is enabled before the DTLS tunnel is established and is needed for routes/filters enforcement), to ensure optimum performance. If the DTLS tunnel cannot be established or it is dropped at some point, the client fails over to TLS and adjusts the MTU on the virtual adapter (VA) to the TLS MTU value (this requires a session level reconnect).

Block UDP (in & out) for VPN client in Windows Firewall

C:Program Files (x86)CiscoCisco AnyConnect Secure Mobility Clientvpnagent.exe





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