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https://support.google.com/a/answer/6374496?hl=en
See the Hosted S/MIME FAQ for additional information about client support and enhanced encryption. ... You can also use the Gmail S/MIME API to manage things like viewing, deleting, and setting default user keys. Users you allow to upload certificates can do so in Gmail settings.
https://www.xda-developers.com/gmail-v7-2-prepares-to-add-support-for-smime-enhanced-encryption/
Gmail v7.2 Prepares to Add Support for S/MIME Enhanced Encryption. If there’s one lesson everyone learned thanks to a certain high profile election, it’s the importance of e-mail security.Author: Mishaal Rahman
https://webapps.stackexchange.com/questions/13802/how-can-i-get-gmail-to-support-s-mime
Check Penango, it's "the successor to Gmail S/MIME". (Edit - Dead link to old index page replaced by download page for version for free Gmail. Support for Google Apps and paid-for Gmail is a pay-for product.) Penango makes secure e-mail easy to use, simple to manage, and accessible everywhere.
https://www.tomshardware.com/news/google-hosted-smime-gmail-encryption,33582.html
Google adopted S/MIME encryption for the enterprise version of Gmail, but it comes with a compromise: The encryption is no longer end-to-end, and Google can decrypt all S/MIME emails.Author: Lucian Armasu
https://support.google.com/mail/forum/AAAAK7un8RUl0fiRvI6u4M/?hl=en
S/MIME support for Gmail. Fossa Guard is a Chrome extension to compose and to send S/MIME on Gmail ... 7/24/16. falcon52. Do you really support attachments (as per screenshot)? And what about Gmail's auto-saving? 7/24/16. Original Poster. Fossa Team. Yes, attachaments supported though limited by 100KB for the moment (beta).
https://support.google.com/a/answer/7307532?hl=en
Hosted S/MIME is supported when sending email using Gmail clients from Google for web and mobile devices and other clients, such as IMAP. If you send a message using the other clients, Gmail will add the S/MIME certificate, sign the message and encrypt it if possible.
https://security.stackexchange.com/questions/159144/receiving-s-mime-signed-emails-with-gmail
Gmail mangles S/MIME signed only messages. Before 2017 it was done for multipart/signed from summer 2017 it has started for signed-data as well. Looks like it's done in a favor of G Suite subscribers and there is no hope that Gmail team will fix it.
https://support.google.com/a/answer/7280976?hl=en
Use S/MIME metadata attributes in expressions. You can make sure that certain messages can’t be sent or received unless they are S/MIME encrypted or S/MIME signed. You do this by creating a content compliance expression using the S/MIME encryption or S/MIME signature metadata attributes. Then, you set up how messages are handled.
https://www.esecurityplanet.com/views/article.php/3910181/Simple-Steps-to-Securing-Email-with-SMIME.htm
Oct 27, 2010 · For one, the major webmail clients, including Gmail and Hotmail do not have built-in support for sending or receiving messages with S/MIME security features. One workaround is to use a …
https://support.google.com/mail/answer/6330403?hl=en
S/MIME is used to support enhanced encryption in transit, and automatically encrypts your outgoing emails if it can. Important: These steps only work if you have S Gmail Help
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