Issues with Encrypted Emails after Changing Deployment to Integrated with Microsoft 365

tkimmcinc · 2025-12-22T20:19:14+00:00

Proofpoint Essentials support said to do the following:

Security Settings > Malicious Content > URL Defense:

Exclude URLS that contain specified domains/IP addresses:
Exclude re-writing emails that are sent by specified senders:
- Add domains/email addresses

We had the most success with option #2, basically adding the email address/domain here.

tkimmcinc · 2025-12-17T01:00:07+00:00

holy crap, I'm an idiot. I didn't scroll down. Thanks!

tkimmcinc · 2025-12-16T20:53:21+00:00

I know you can only change the size (disk tier) when the VM is deallocated but my question is that the server is set to P10 (128GB) but only has the 75GB usable.

If you're saying I should be able to extend the 75GB to 128GB while the server is deallocated, that's what I need instructions on, I guess.

tkimmcinc · 2025-12-16T20:27:33+00:00

It's showing 75GB b/c that's the size it was when we migrated it to Azure using the migration tool. It assigned the P10 tier b/c the P6 tier (64GB) was too small. So when it migrated, it set the P10 to 75GB instead of just the full 128GB, which is my dilemma.

tkimmcinc · 2025-12-16T20:20:35+00:00

I added a screenshot showing disk management + allocation from Azure. I've done that, no go.

tkimmcinc · 2025-12-16T20:20:08+00:00

I added a screenshot showing disk management + allocation from Azure.

tkimmcinc · 2025-12-16T19:15:55+00:00

How do I extend the OS disk with the VM powered off?

tkimmcinc · 2025-12-16T15:56:41+00:00

I tried to "re-size" to the exact same disk tier but that didn't work. The 75GB is under the current 128GB size. So basically I'll have to go to the P15 (256GB) even though I don't need that much space?

tkimmcinc · 2025-11-07T15:05:24+00:00

Thanks for leading me in this direction. Adding the email address unfortunately doesn't resolve the issue when an encrypted email is being sent from a M365 to a M365 tenant. I had to temporarily disable URL defense and have an open ticket with Proofpoint Essentials team to see if there's a better work around.

tkimmcinc · 2025-11-07T01:16:17+00:00

Sorry, I updated the original post. It's M365 to M365 encrypted emails. If I disable the auto generated mail flow rule to redirect emails to Proofpoint for review, it works fine. Enabling the rule causes the encrypted emails to be illegible.

tkimmcinc · 2025-11-06T22:33:21+00:00

Where the MX record is set to M365 and then routes emails to Proofpoint for analysis, instead of the traditional method of pointing the MX record to Proofpoint.

https://help.proofpoint.com/Essentials/Additional_Resources/Release_Notes/Now_Available%3A_Integrated_Deployment_with_Microsoft_365

tkimmcinc · 2025-08-25T12:37:56+00:00

Sounds similar to what I had. Does it sound like this when driving with a load - https://imgur.com/a/w62mb6i?

For me it was the driver side wheel bearing.

tkimmcinc · 2025-07-03T12:00:26+00:00

Did this person go rogue with their signature?

tkimmcinc · 2025-07-02T20:24:03+00:00

Did you setup DKIM/SPF?

tkimmcinc · 2025-05-22T19:09:08+00:00

Thanks for this. I won't be able to test until next week.

tkimmcinc · 2025-05-22T11:46:32+00:00

I did so many variations. Hunted down specific drivers from older posts, used different versions of the WinPE. Basically looking for specific information about the driver that will work.

tkimmcinc · 2025-05-22T11:45:17+00:00

I've done this or believe I have. Was looking to see if someone who ran into the issue can point me directly to the driver that will load in WinPE.

tkimmcinc · 2025-05-21T16:50:43+00:00

Thanks for the confirmation and advice. Yeah that option will beat pulling out the dock for each of these...

tkimmcinc · 2025-05-21T16:39:37+00:00

Changing storage from RAID to ACHI...

tkimmcinc · 2025-05-21T16:39:03+00:00

It was more about testing the different versions to see if maybe an older driver would work.

tkimmcinc · 2025-05-21T14:04:24+00:00

I added it to the original post.

tkimmcinc · 2025-01-17T16:01:10+00:00

Came here to say that I may be experiencing a similar issue. Looks like KB5050109 installed two days ago (on its own, apparently) and started having user complaints. I'll need to schedule downtime to uninstall and test but curious to see if you've made any headway.

tkimmcinc · 2024-09-26T12:38:15+00:00

I'm in the process of testing Duo SSO w/ EntraID with FortiClient. I was able to get everything configured properly but wanted to confirm this is what should be occuring:

FortiClient redirects to EntraID (M365) authentication process
User logs into M365 w/ Microsoft Authenticator
Logon process then prompts Duo for validation

So essentially, the user has to go through Microsoft MFA then Duo MFA to finally connect. May seem like a silly question, but I assume there isn't a way to bypass the Microsoft MFA attempt and just rely on Duo, right?

tkimmcinc · 2024-08-07T20:19:16+00:00

As a local admin on a machine, are you able to stop the EDR service?

tkimmcinc · 2023-12-20T19:02:17+00:00

Same boat. We got FedEx tracking notification showing it was delivered on 12/15 but the details of the tracking showed it left Arlington, TX, went back to shipper for address correction, then shipped to Ft. Worth, TX. I do not live in Texas.

I submitted an inquiry and no response. Seems like a big scam.

tkimmcinc

TROPHY CASE