signtool.exe fails with: "SignerTimeStampEx2() failed." (-2145844844/0x80190194) when signing executable

I'm using signtool to sign an executable on Windows 10, using a GlobalSign certificate. This has worked like a charm for years. Recently it has stopped working. Using the following command line:

signtool.exe sign /a /v /n SomeName /tr http://timestamp.globalsign.com/scripts/timstamp.dll some.exe

I see that the correct certificate is selected, but then get the following error message:

Error information: "SignerTimeStampEx2() failed." (-2145844844/0x80190194)
SignTool Error: An unexpected internal error has occurred.

Any idea what it means and how to fix it? The Microsoft Documentation unfortunately does not list any error codes.

I had the same issue. I think the Globalsign server may have been upgraded at some point and now needs different parameters for signtool.

See: https://support.globalsign.com/code-signing/code-signing-windows-7-8-and-10

Not sure if all these steps were needed but this worked for me:

1. I re-issued the certificate
2. I changed the timestamp url to: http://rfc3161timestamp.globalsign.com/advanced
3. I added: /td SHA256
4. I removed the reference to the cross certificate

See: https://support.globalsign.com/code-signing/code-signing-windows-7-8-and-10