Recently, I have noticed that when I send an email to a Gmail account from Outlook 2016, the recipient sees a question mark next to my email address as follows:
The question mark only appears when I send an email from Outlook 2016. When I send an email directly from the Webmail/Server, the question mark does not appear. Thus indicating, the issue likes within Outlook 2016.
Upon reading up on the matter, I have come across a few articles citing the issue lies with the Authentication issues. In other words, I need to assign a Digital ID to the outgoing email(s), so that the recipient is able to verify that the email came from myself and has not been tampered, after it has left my Outbox.
In order to obtain an email certificate, I headed over to Comodo. Here, I downloaded the Email Certificate and installed it on my Computer, by simply following the Import Wizard, as follows:
I then headed over to Outlook > Options > Trust Center > Trust Center Settings > Email Security and saw that the Email Certificate had been auto populated as follows:
As far as I am aware, this is all I have to do in order to 'activate' the Digital ID and thus Authenticate the emails. Do I need to select the 'Import/Export' button, under 'Digital IDs (Certificates)', and modify additional Settings? If so, I am not sure on the relevant steps as I just seem to go around in circles with the Import/Export process.
I then head to create a new email, ensuring the following are selected in the Ribbon:
Despite following the above, I still get the question mark in Gmail, stating that I still need to authenticate the email.
Is anyone able to see where I may be going wrong here?