Outlook connection issues

[SeetendraPanda]

Hello Everyone
we are facing an issue with Microsoft Outlook taking a lot of time to connect to the server and getting e-mails.
This is happening to a lot of users especially when they are waking the mac from sleep and once VPN is connected it takes outlook close to 3-4 minutes to get the e-mail to flow in.

This is not an issue with the Windows machines in our environment. They work just fine.
We opened up case with Microsoft but no luck. We even gave them Wireshark logs but no luck.

The different versions of we outlook tried
16.37 16.40 16.41

Any help on this please.

This does not happen when we close the outlook application completely and open it again. It connects immediately when we do this step.
Same is the case with powering on the mac and then opening up outlook.

[SeetendraPanda]

@pbowden Hi Paul any help on this please.

[rqomsiya]

We’re seeing the same issue here. But our issues persist even after a cold boot or fresh open of Outlook.

Basically we are seeing issues around persistence of Outlook when on VPN. We notice that Outlook status changes from “Connected to xxx server” to “Connecting to xxx server”. We see this happen at least a few times per hour.

Our network team has been unable to find any drops on our FW.

Note: We are on prem exchange hosted.

[SeetendraPanda]

We are not on prem but we are seeing the same issue. looks like outlook is hiting the some servers and then getting redirected.
i hope Paul can help us find the solution for this issue.

[rqomsiya]

Agreed.. I know our Windows side is experiencing this as well. Hoping @pbowden has seen this with other customers.

[SeetendraPanda]

@pbowden any update on this please. This is a CEO level issue for us and causing a lot of issues.

[talkingmoose]

@SeetendraPanda, do you have your Exchange servers exposed to the internet where Outlook can connect using Outlook Web Access (OWA)?

Normally, Outlook takes just a few seconds to connect. When you mention VPN, that leads me to begin looking at that. I suspect the time to reconnect may be due to Outlook's Autodiscover feature, which attempts you to connect to the correct server. Sometimes, that's not configured well. For example, if Autodiscover is configured for your external DNS, but directs clients to internal server addresses, that would explain the lag when connecting over VPN.

Or VPN may be hindering Autodiscover.

Ideally, Outlook would connect to one of your OWA border servers if your Macs are outside your network.

[SeetendraPanda]

Can you help me in understanding how can I find this? Do I get in touch with the exchange guys to give me this information since I am not sure on the infra on the outlook side?

I will pop up this question to the exchange guys and see if they have an answer.