Why would a digitally signed executable be treated as unsigned until viewing certificate details
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I'm getting a very odd result when running an executable that has been digitally signed.

The executable was signed using signtool.exe using a proper level 2 code signing certificate (not self-generated).

Testing on a Windows 7 machine, if i launch the signed executable, I get the windows warning dialog saying Publisher Unknown (i.e. not signed).

However, if i then cancel and right-click on the executable and go to Properties -> Digital Signatures, the Signature list shows the signed certificate, which i can then click on and choose "Details" to view the details of the signature, which is shown as "The digital signature is OK".

At that point, if i launch the executable, now all of a sudden windows properly recognizes that the exectuable is signed and reports the correct "Verified Publisher".

It seems like maybe Windows wasn't checking the certificate online until i went to view the actual certificate details from the properties dialog of the executable (note that it wasn't just a delay after launching the executable, it doesnt matter how long i wait or how many times i launch it, it treats it as unsigned until i go into Properties / Digital signatures of the file).

This a generic Windows 7 install I use for testing -- it hasn't been modified or tweaked in any way.

This behavior seems to defeat the main purpose of code signing on Windows-- how can it be that the executable is treated as unsigned unless the user knows to go into the right-click properties and digs around for a certificate.

Is there something I'm missing? Some way to mark the executable as one that Windows should actively go check the certificate of when executed?

Ovenbird answered 7/12, 2010 at 18:4 Comment(2)
Have you managed this issue? I am facing the same thing?Fidole
I have also observed this. Sometimes, if I just leave it a few minutes, running the program again shows the validated "blue" dialog. But I have also observed viewing the sig 'fixes' it.Myth
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Most likely OCSP revocation couldn't be checked automatically for whatever reason (connectivity problems etc). You need to perform the tests on more systems in order to narrow down the problem.

Annelieseannelise answered 9/12, 2010 at 7:46 Comment(1)
I also originally thought it might be a problem connecting to check certificate. But the fact that it has no problem at all checking and reporting on the certificate validity once you go into properties and view the details of it (and thereafter shows the certificate as valid), seemed to rule out that possibility.Ovenbird

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