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I'm using gmail from work, but I need to enter a password for a proxy when accesing the first web page. The password is asked from inside the browser. I receive a certificate from the proxy which I must accept in order to make the Internet connection work.
Can my HTTPS connection, between gmail and browser, be tracked in this situation?
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This doesn't make you impenetrable to MITM attacks, but it makes life much harder for crooks and will likely cause them to look for an easier target. As with VPNs, HTTPS websites encrypt data and prevent attackers from intercepting communications.
While HTTPS sessions can be reliably considered secure from eavesdropping attacks, HTTPS by itself does not protect against any other types of attack.
As explained in the introduction, to be sure that a man in the middle cannot read the packages, SSL was invented. The messages are now encrypted with a key that only the client and server know of. Though it is still possible to do active eavesdropping on a secured connection.
It protects against man-in-the-middle attacks, and the bidirectional encryption of communications between a client and server protects the communications against eavesdropping and tampering. The authentication aspect of HTTPS requires a trusted third party to sign server-side digital certificates.
Fiddler describes it like this:
Q: The HTTPS protocol was designed to prevent traffic viewing and tampering. Given that, how can Fiddler2 debug HTTPS traffic?
A: Fiddler2 relies on a "man-in-the-middle" approach to HTTPS interception. To your web browser, Fiddler2 claims to be the secure web server, and to the web server, Fiddler2 mimics the web browser. In order to pretend to be the web server, Fiddler2 dynamically generates a HTTPS certificate.
Fiddler's certificate is not trusted by your web browser (since Fiddler is not a Trusted Root Certification authority), and hence while Fiddler2 is intercepting your traffic, you'll see a HTTPS error message in your browser, like so:
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