Outlook.com against Mutt
 

Good morning.

There will be a question at the bottom. Go there, if this is too lengthy.

I do not consider this topic well placed in any of the existing LQ forums. It is network-related, security-related, Microsoft®-related, I am dealing a problem of ill-education and servitude in obduracy as well as immunity to learning.

I am not trying to “solve a problem”. It is too late for that.

What I need is clarity.

The situation:
Some of my mails are not read by an addressee who is using an outlook.com (ex hotmail) account, unnecessarily via a webmail-interface.
The reason given is none. I can have the statement “I see that you sent me a mail, but I cannot read it”

No error-description is available, and I must consider any inquiry in that direction futile, as is my proposition to ask the support of the mail-service for help.

Needless to say, this happens with arbitrary messages, containing attachments or not. All my mails are in plain-text.

There are two details, that I consider important, although I cannot claim to understand if they are significant in the context:

1. Systematically and for ages, I sign all my mails with GnuPG. Detached ASCII, i.e. a plain-text attachment, like this:
   
   Quote:

   Content-Type: multipart/signed; micalg=pgp-sha512; protocol="application/pgp-signature"; boundary="zx4FCpZtqtKETZ7O" Content-Disposition: inline

2. Before the replacement of hotmail by outlook.com, such difficulties have never been reported in years.

The addressee does not appear to be aware of changes related to the mail-hosting, nor the simplest facts about mail and I am unable to continue trying to explain any possible causes of- or remedies against the phenomenon which causes me much trouble. My hints, so far, are ignored completely. It is a God-given fact that some of my mails are problematic.

I am obliged to communicate regularly with the same person and to even transmit file-attachments.

Only once, a binary attachment had been mentioned as the source of possible mischief, as I could receive a response to my mail anyway...

Question: Can a detached digital signature cause sporadic trouble on the receiving end, if the (1 and only) user gets his mail via the outlook.com Web-Interface?

There is no need for a better procedure, as, at this point, I seek a more permanent solution.

I doubt that an attachment could affect the readability of the body of the email unless something really strange is going on.

I've not had anyone who I send emails with Mutt make any such complaints, but I have no idea whether any of them are using webmail. One of my daughters still uses a Hotmail address.

What encoding are you using in your emails (UTF8 or something else)?

Can your correspondent send you a screenshot of one of the borked emails?

Can he forward one back to you so you could inspect it?

I have an idea for testing, if you have webmail access of your own (I have webmail access through my ISP, but I almost never use it). It's not a great idea, admittedly, but I think it's worth a shot. Try copying yourself on emails to this person, then taking a look at them in your own webmail, particularly the ones about which you receive complaints.

You could also sign up for an outlook.com account and bcc every email you send to them with it. When they have trouble visit your oulook account for the same symptoms.

Thank you for your responses.
Of course, I can try to resolve a problem, if there is one. But the fact is not established. As far as technology is involved, I hope to recognize a potential pitfall, a proven fact or to exclude them. The question of used encodings is a good start...

US-ASCII, iso-8859-15 or UTF-8.
I checked one of the “problematic” mails and it was, in fact, encoded as US-ASCII. No attachment there.

I am gnawing my fingernails on this question, but might give it another try. Before I was sure that the mailbox is accessed via web-browser, I had asked which mail-client were used (« client mail », I master the french language enough, even for such tricky technical questions). Then, the response was “I do not understand any of your questions”. There is even a French expression for screen shot. I fear a nervous break down before I can have one.., but maybe I am lucky. Yes. I will include the suggestion in my next mail.

dto.

In fact, me too I can access my mailbox via web-mail and actively ignore the possibility.

A promising procedure.
Although I consider myself blameless, I should at least once verify how outlook.com deals with my own mails. The perspective to render support to a person who shows no interest to comprehend a system that I do not care to know, myself, is however rather annoying.

I have tried several times, since this last post, to get an outlook.*. or hotmail.com-account, but the site is reported on maintenance, the moment that I send the inscription. Every other way to reach a higher level of enlightenment gets priority, now... (I am out of beer, too).