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Sure! I don't mind.

> The MX records store the server receiving mail (i.e. an smtp server). How does this relate to the imap server?

My IMAP and SMTP server happen to be hinding on the same IP, which is mentioned in the MX record. Inky seems to have detected this. Port scanning? Trying common names like smtp.$domain and imap.$domain ? I'm not sure how it does this, but someone got very frustrated when coding it :) and it works quite well as a result.

> In my experience, these [unsubscribe] links dont usually work and the better solution is to forward all mail from that source directly to junk mail. Is your experience different?

I'm not sure how Inky discoveres the presence of an unsubscribe link, but the experience is outstanding. Here's a quick walkthrough. Say I want to unsubscribe from this message: http://i.imgur.com/XlB3X.png

This message happens to contain a "List-Unsubscribe: <http://.../>, <mailto:unsubscribe@...>" header, but lots of the ones in my mailbox do, so either it's common or Inky has other special sauce going on.

After clicking the unsubscribe button, it offers to unsubscribe via "automated email" or "via the web": http://i.imgur.com/c7KXj.png

If I click the first, it offers to send this message for me: http://i.imgur.com/c63fY.png

If I click the second, Chrome pops up with the unsubscribe link: http://i.imgur.com/DUGGk.png

I don't know if this works just for messages with a List-Unsubscribe header or if it's scanning the body text of the email. For the record, that mail had "If you do not wish to receive further communications like this, please unsubscribe [here.]"

Other mail clients: Please copy this mercilessly!

> Do you actually use these? Do you really care how long a message is cached for?

Sure, they're confusing for average users; that's why they're in the settings. No average user ever opens the settings, but I like that they're there. They've thought about a lot: if I send mail to people who use terminals and text-mode email all day, I appreciate being able to turn off settings like "Convert dashes to unicode characters" and "Convert emoticons to images as you type." Lots of people who use mailing lists will gladly appreciate the "Put new text below quoted text in replies (bottom-post)" setting. And I can turn off sounds and notifications so I don't get distracted by my mail client.

Yes, having these really does provide value for advanced users. (Erm well, for me anyway)

>> Didn't interfere with my other email clients, as promised

>Is this an issue? How does this happen?

I've tried mail clients that download all the mail, mark it all as read, and then promptly delete it from my server's inbox, either due to misconfiguration or poor design. Inky is a "thin" IMAP client, so there's no reason to add much client-side state. Everything you do to a message is immediately applied to that message as it exist in the server's copy -- marking it as read, moving it around, and so forth. This has the disadvantage that it probably won't work if I disconnect, but I like the uncompromising philosophy of not touching my mail unless I tell it to.

> What is the average users response to such a warning? Heck, would you know if there were a MITM?

It's the burden of the mail client to word the warning in such a way that it tells users what's happening without scaring them away. For example, I'd love if clients say something lighthearted in the warning message like "If you're at a coffee shop right now, please wait until you get home to check your mail; something phishy could be going on..." to give people an intuition of what they should do while encouraging them use their heads.

The reason why people trust PKI more than they should is because we teach them to click through scary certificate warnings. Thunderbird throws "UNTRUSTED CA" jargon at your users' face. They just want to check their mail, so before long, you've conditioned to treat the "Confirm security exception" button as a "Make my problem go away" button. It takes them to your inbox without any visible consequences, so they think to themselves that the scary certificate warning must not have been a big deal.

Still, though, any warning is better than nothing. At least if someone's account gets stolen because they clicked through a PKI warning, they might have some idea when it happened.

Right now, Inky does not warn me if I add a NEW server with a self-signed SSL cert. If an attacker can be there right when I'm setting Inky up, I've just given him my password. (Read dmbaggett's security clarifications elsewhere in the thread though; it's not as bad as I originally thought it was)

Wow, thanks for the insight and the effort in the response!

> terminals and text-mode email all day, I appreciate being able to turn off settings like "Convert dashes to unicode characters" and "Convert emoticons to images as you type."

Emails are normally sent with a mime type of multipart/alternative with two subtypes of text/plain and text/html. Therefore, for your terminal using friend it would simply look at the text/plain version instead of the html version. Im sure you already know this, but what I am trying to illustrate here is that I believe that all of these details should be managed by the technology as in this case: the client which has a hard time displaying images etc should use the text/plain version.

> "Put new text below quoted text in replies (bottom-post)" setting.

This is interesting. I remember when I was in a corporate network I got about 300 emails/hour from one mailing list. Now, the client I was using then had a view that looked like a forum where you could see an email and its responses below and indented. When I wanted to follow a thread, having bottom posting was annoying because I'd have to scroll through the quote. On the other hand, If I were jumping between threads, then it was useful. I wonder if there might be a better approach which separated the quote from the response and allowed the client to display the quote when necessary.

Do you understand my line of thinking or am I entirely crazy? Are there any options that you feel cannot or should not be managed by the client? Do you believe in this idea that the client should do as much as possible?

As far as the security stuff, I'll try to break down my thinking.

Variables to account for: valid/invalid, same as known/different from known, self signed/trusted signer/untrusted signer/unsigned.

Errors in each variable mean different things and have a different chance to occur under normal conditions. For example, if the cert is plain invalid (e.g. the trusted signers signature is incorrect) this almost certainly indicates malice as opposed to the cert being different than what is currently known. This is opposed to having an untrusted signer or a self signed cert where it is possible (and almost likely) to have occurred either out of ignorance of the issuer or their simple denial to pay large sums of money for a valid cert. Furthermore, it isnt entirely uncommon for servers to switch their keys due to some security hole such as a problem in the key generation algorithm. Since the PKI provides no express way to state: this server is switching its keys, we simply take it on faith. You might think that this is unnecessary since we trust the signer, but CA's have been compromised before.

The problem of no visible consequences I feel is also mishandled. If you get the initial warning at a cafe and you click through and then later at home, you get a trusted signer different from what you had at the cafe, a warning should pop up that your information was probably stolen at the cafe so you can at least change your passwords.

There is a hidden problem here of dns hijacking. This is actually done commonly at "pay-for-your-wiki" places. They do not have the intention of stealing your information, but they will case security problems since they will pretend to be google.com or whomever else until you pay for the internet. I suppose that the browser should check the entity of the cert and if different from the requested entity, treat it as a redirect. This whole situation, however, requires more thought.

All in all, I feel like technology is burdening the user by trying to make the user understand the technology and not the situation. Sorry if I rambled too much, but what do you think?

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