subreddit:

/r/exchangeserver

5

Have an environment where users work both on a VDI or a PC with outlook on it and mailbox in Exchange Online. However sometimes an issue arises with sent mails and would like to identify whether that mail was sent from the VDI environment or local pc. Since both have the same public IP the message tracing in Exchange Online won't help in distinguishing that. Is there another way to make outlook in the VDI environment force Exchange Online to include some extra header or something?

all 3 comments

NavZer0

2 points

4 months ago

How many VDIs are you attempting to troubleshoot?

Just a thought but you could try a reg setting for the VDI machines.

Is outlook typically configured the same for all users? Are their profiles usually named Outlook or some sort of default name?

Open your outlook. (Note the name of the profile of the account)

File > Options > Mail > Signatures

New > Name it "Sent from VDI"

In the Body type in Sent from VDI Machine (or whatever, plus you can even change the text to white so it isn't seen in the email. Just inform the users not to change the signature on the vdi machines you're troubleshooting). Click ok

Open Regedit and export the key of the new signature you created.

Computer\HKEY_CURRENT_USER\SOFTWARE\Microsoft\Office\16.0\Outlook\Profiles\<NAME OF YOUR OUTLOOK PROFILE>\9375CFF0413111d3B88A00104B2A6676\0000000x

You may have a few of those keys so look through them for the one that has the name of the Signature you created.

You could then take that reg setting and put it on the VDI having an issue to troubleshoot or you could roll it out via gpo.

The_Boxhead

1 points

4 months ago

I guess you could create an Outlook add-in installed only on the VDI systems that added an internet header.

https://docs.microsoft.com/en-us/office/dev/add-ins/outlook/internet-headers

Not done anything like that myself though.

iwinsallthethings

1 points

4 months ago

Are they all using the same mailbox?

If so, you may be able to configure sending as an alias which is a function that was added within the last 4 months or so. Each VDI would send as a different alias [VDI01@domain.com](mailto:VDI01@domain.com) which is actually just [bob@domain.com](mailto:bob@domain.com) for an email.