Thank you for your reply. Yes it is StandAlone SMS / GW with HTTPS inspection enabled. Cpview looked okay from what I could tell.
Browsing office.com as my testing I noticed the bellow observations, the left image is with HTTPS inspection, the right is without.
![office.com error.jpg office.com error.jpg](https://community.checkpoint.com/t5/image/serverpage/image-id/17725i2DCEF7A567BB868D/image-size/large?v=v2&px=999)
![office works.jpg office works.jpg](https://community.checkpoint.com/t5/image/serverpage/image-id/17726iBCB3E72E9F617826/image-size/large?v=v2&px=999)
The custom HTTPS bypass rule does not appear to be working, I have added portal.office.com and office.com and it still inspects them. The financial services rule is working in that I could connect to banking sites with no issue.
I tried a local news website, and it connects fine, the certificate shows issued by and the name of the HTTPS inspection certificate "client.com"
I observe the following log in the Man Server:
![detect.jpg detect.jpg](https://community.checkpoint.com/t5/image/serverpage/image-id/17727i708D4929115F5F8D/image-size/large?v=v2&px=999)
I have had a look at sk159872, which doesn't seem to give me any help, I updated the Trusted CA list on the smartdashboard with Checkpoint support yesterday. I have added the https inspection certificate to this list and it has not helped. I have observed a fair number of Microsoft URL's failing with Untrusted Certificate.
I am waiting for more feedback from Checkpoint as to what to check next.