[Last Call] Learn about multicloud storage options and how to improve your company's cloud strategy. Register Now


S/MIME - User receving "Problems Encrypting" Error

Posted on 2010-09-21
Medium Priority
Last Modified: 2012-08-14
I have a user that is having issues sending a file that needs to be encrypted to anyone outside the company.  The encryption tool being used is S/MIME.

When she attempts to send the file via outlook to someone outside the company, she receives the following error message:

"Microsoft Office Outlook had problems encrypting this message because the following recipients had missing or invalid certificates, or conflicting or unsupported encryption capabilities"

The weird thing is that she is the only one having this issue as two others using the same tool are having no issues what so ever.  IT should be known that all systems are win7 /w office 2007.  

One of the guys in our security group who installed the program thinks outlook should be reinstalled, but says he really isn't sure what the issue is.

Any help on this would be appreciated.


Question by:Mangi05
Welcome to Experts Exchange

Add your voice to the tech community where 5M+ people just like you are talking about what matters.

  • Help others & share knowledge
  • Earn cash & points
  • Learn & ask questions
  • 2
  • 2

Accepted Solution

cmartell earned 2000 total points
ID: 33731277
Are you sure she has the recipient's certificate? If she doesn't she will have to add it to the contact info.  To do that she must receive a digitally signed email from the intended recipient, then she will have to right clck the name in the From box, and then click Add to Contacts on the shortcut menu.  Only then will she be able to send that person an encrypted email.

Author Comment

ID: 33731411

You might make a great point.  It should be known that this user just had her machine migrated from XP to Win7.  Since that time she has not be able to send these documents to any recipients.  This is the only application IT does not manage as this is something security handles completely.  The security guy is not sure what the problem is, but this makes sense.  With a new image, all the previous certs are gone.  I will work with the user tomorrow and respond back with an outcome.  Thank you for your help.  Stay tuned.  

Author Comment

ID: 33740068
Spoke with the user today.  She said that she has tried to add the contact information and has received a digitally signed email from the intended recipient.  She has added the certificate and all would seem fine until she goes to send something to the user.  She would then check the cert for the particular user and it would no longer exist.


Expert Comment

ID: 33740464
Did you verify that she did the import correctly?  Maybe she started the import then when she was asked if she wanted to replace the existing contact with this new information she said no fearing she would lose her contact.  I would have her do it again and watch.

Featured Post

How to Use the Help Bell

Need to boost the visibility of your question for solutions? Use the Experts Exchange Help Bell to confirm priority levels and contact subject-matter experts for question attention.  Check out this how-to article for more information.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

If you thought ransomware was bad, think again! Doxware has the potential to be even more damaging.
Ransomware is a growing menace to anyone using a computer or mobile device. Here are answers to some common questions about this vicious new form of malware.
The Email Laundry PDF encryption service allows companies to send confidential encrypted  emails to anybody. The PDF document can also contain attachments that are embedded in the encrypted PDF. The password is randomly generated by The Email Laundr…
With Secure Portal Encryption, the recipient is sent a link to their email address directing them to the email laundry delivery page. From there, the recipient will be required to enter a user name and password to enter the page. Once the recipient …
Suggested Courses

656 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question