When sending a secure email you might get an "Error sending email!" or the add in options might remained grayed out after adding the recipient's email.
Problem
The Gmail Add in might need to be refreshed or there are pending Chrome updates.
Resolution
To correct this issue, you will need to check that Chrome is up to date and to refresh the add in:
1. Click on the 3 vertical dots to open Chrome Options.
2. Click on Help.
3. Click on About Google Chrome.
4. If it shows pending updates or that it needs to relaunch to finish installing updates, please do so until it shows that is up to date.
5. Click on the 3 vertical dots to open Chrome Options.
6. Click on Extensions.
7. Click on Manage Extensions.
8. You will see the DeliveryTrust add in listed there, depending on your browser settings, you might have the option to refresh or reset, if that is the case, please do so. If not, then toggle the extension off and then back on.
9. Go back to the Gmail tab and refresh the page.
10. Go to the add in Settings and log back in.
You should be able to send secure emails once the steps are completed.