Device: ASA 5505 (Remote Access VPN) Office365 Not Connecting in Outlook

[travis.atherstone]

Hi guys,

We have a scenario where we've inherited a client with the above mentioned device,  inherited a VPN issue with a particular user. None of us here are particularly versed with the Cisco ASDM 6.4 console so would like guidance.

The symptom:

When connecting to the VPN, opening up Outlook in online mode, takes forever, either times out or eventually connects, but takes forever.

I would like some guidance on how to troubleshoot an office365 issue or configure the VPN to work with Office365 and Outlook. They are using Office365 online.

I can ping outlook.office365.com when connected to the VPN. The fact that it eventually connects suggests maybe not a port issue?

I noticed if pinging 8.8.8.8 I get a lot of dropped packets.

Can you help?

Thanks,

Travis

[Marius Gunnerud]

To help you further we would need some more information about your network.

• Is this an AnyConnect VPN or an IPsec remote access VPN (legacy)
• is all traffic being tunneled or is split-tunneling configured
• is there connectivity issues to local resources behind the ASA5505 or just when going to the internet.

Also, would be helpful to see a full running configuration (sanitized).

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[travis.atherstone]

Hi Marius,

1. It's AnyConnect VPN.

2. I went into Group Policy (just googled split-tunneling as wasn't sure) - please see attached.

3. They are able to connect to network drives without issue. It just seems when trying to establish a connection to Microsoft Online/Exchange in Outlook.

Can you advise on safest way of providing running config - or a snippet of it, a bit concerned I will not sanitise properly.

Thanks.

[Marius Gunnerud]

We would also need to see the access-list SPLIT

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[travis.atherstone]

Hopefully, this is what you want. (see attached)

[Marius Gunnerud]

Do you have a local Email server that reaches out to office365 or do your clients go directly to Office365?

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[travis.atherstone]

Hi Marius,

I posed this question to the people responsible for managing their e-mail service, unfortunately we don't have visibility of this.

They said they previously had an on-premise exchange and were migrated across to Office365, but also said it didn't go very smoothly and say they still receive errors in the cloud to do with on-premise syncing. I noticed myself that the domain account when logged is able to auto-discover the mail profile against the AD account, this is usually reminiscent of Azure AD syncing upto cloud. I've gone back to find out more.

Not sure if this is a VPN issue or something to do with the mailbox itself.

Kind Regards, Travis

[Marius Gunnerud]

From the sounds of it, to me it seems like a mailbox / office365 issue.

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