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RhoSysAdminFlag for United States of America

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Can electronically sign a doc in Word 2010, but NOT in Word 2016 (same certificate)

I have a user certificate that I use for electronic signatures.  I can use it to sign Adobe PDF's, and Microsoft Word docs in Office 2010 (Windows 7).

When I try to sign a similar Word doc in Office 2016 (Windows 10), I get the following error :

Your signature could not be added to the document.  If your signature requires a smart card, ensure that your card reader is installed correctly.

I get a failure whether the Word doc is on a network share or on my local drive.

The same certificate on the same Windows 10 computer can electronically sign a PDF.  

I get this error on multiple Windows 10 computers (using the same certificate). I even made sure on one Win 10 desktop to make sure a new user profile was created when I logged in.  

A coworker who also has Office 2016 running on Windows 10 can sign a similar doc (located on the same network share) without any issues.

I have revoked and re-issued myself a new certificate multiple times.  But I don't think it's the certificate since it works just fine on every Win 10 computer if I signe something in Adobe Reader.

It's only Word 2016.  

Where do I look for the red flags?
Avatar of Peter Hutchison
Peter Hutchison
Flag of United Kingdom of Great Britain and Northern Ireland image

Where did you get the certificate from? An internal CA server or public CA server? Check that root certificate for CA is installed as well as user certificate. Open properties of the certificate and make sure it hasn't expired, that it has a private key associated with it and has a trusted CA root certificate.
Avatar of RhoSysAdmin

ASKER

It's issued by our internal PKI.  I confirmed I have a private key, and it's valid until 2024, and "path" is good when you look at the details.

Again - this cert works fine when signing a PDF through Adobe Reader, or signing a Word doc in Word 2010 on a Windows 7 computer.  My issue is limited to Word 2016 on any Win 10 computer.
I depends on the kind of certificate you are using. Check the following requirements when developing a custom CSR:
Public Key length: 2048
Signature hash algorithm: sha256
Key usage: Digital signature, Key Encipherment (a0)
Enhanced Key Usage: EFS, Secure Email, Client Authentication.
Subject: CN = username, E= Email address
Template Name: User

I then tried signing a document using the above on a Word 2016 document and gave no errors or warnings.
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