8
votes
3answers
1k views

Why enable SMTP STARTTLS if OpenSSL is dangerous?

There are a bunch of people in the anti-surveillance movement who are virtually demanding that I enable SMTP STARTTLS support in my environment, in order to enable opportunistic MTA-to-MTA encryption. ...
3
votes
2answers
498 views

Test STARTTLS configuration of SMTP server

Is there an easy way to test an SMTP server to check for configuration issues associated with STARTTLS encryption, and report on whether it has been configured properly so that email will be encrypted ...
1
vote
3answers
563 views

SMTP and SSL/TLS

If I understand correctly, communication between SMTP servers may be encrypted but is not required. Because it is optional, does it really have benefits? When server A connects to server B, both of ...
4
votes
3answers
605 views

How do you verify a certificate belongs to a domain?

I'm using PHP and trying to verify a SSL certificate belongs to the SMTP domain/IP I'm connecting to. Currently I can verify the certificate is valid using the following code $resource = fsockopen( ...
1
vote
1answer
857 views

Why is Message Labs sending mail in plaintext?

I have several SMTP servers on various networks around the world, and all of them are getting mail through ESTMPS - extended SMTP using TLS. So the email coming from GMail, MSN, Yahoo, as well MOST ...
4
votes
2answers
1k views

If I send an email over SSL, will it always be transmitted over SSL?

This is largely a question of how MTAs and different components communicate. I'm curious that if I send an email using SMTP over SSL to my MTA, can it's next jump to the next MTA or MDA be insecure? ...
12
votes
3answers
662 views

Can I expect my e-mail to be routed securely?

If I connect to my e-mail server via SSL (SMTP/SSL) and the recipient also only checks his e-mail via SSL (web/https or IMAP/SSL), does this - generally speaking - increase the security for the ...
6
votes
1answer
2k views

Email SSL security?

I use IMAP and I only access my email through SSL. However, the settings for encrypted email access seem a bit more complicated that https. Can someone explain the security implications of the ...
24
votes
4answers
13k views

What steps do Gmail, Yahoo! Mail, and Hotmail take to prevent eavesdropping on email?

I would like to ask what happens when an email is sent from gmail, yahoo or hotmail public web email services? I don't understand email protocols in details, but as far as I know email traffic is ...