This is expected. We stopped signing our installers last year, because it’s an extortion racket. the certificate prices increase every year, and now they switched to a model where yo need to buy/rent a secure token store hardware from them to store the signing keys, and enter a ping code every time you sign something (and we signed a lot of executables per build, and do a lot of builds, per day).
This one I cannot comment on as I’m not familiar eioth Trend Micro; I suggest to reach out to them and report this as false positive, but I’ll also look into this from our end, just in case.
The Suspicious File Blocked message no longer happens, thank you!
On the signing of your installs, I was in the process of renewal at the time I created this issue.
I may agree with you on the price increases, but it just the cost of doing business. I got my cert and renewal at DigiCert and they do have a cloud option to store your keys, so no “hardware”.
I signed over 40 files with no prompt for a “ping code”. It works just like the previous method of signing.