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hotmail.com / outlook.com not working (with autocrypt?) #561

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csb0730 opened this issue Feb 5, 2019 · 12 comments

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@csb0730
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commented Feb 5, 2019

hotmail.com / outlook.com seems not to work!

DC version v0.100.0 from github.

A colleague of mine installed v0.100.0, created a new free account at outlook.com.

Mails sent from v0.100.0 to me without encryption are displayed at my phone (v0.20.0 and Thunderbird with Enigmail).

After I did first reply next mails from v0.100.0 peer are shown as empty mail with two binary attachments (ATT00001, 12 Bytes; ATT00002.bin, 2021 bytes).
Both parts are encoded as “Content-Transfer-Encoding: base64”

No pgp part is seen in message source! No plain text part is seen in message source!
==> no idea about root cause for that behaviour. But message is full of MS specific headers and autocrypt header is not to be seen in headers!

Then switching with same installation to a gmx accout ==> all works fine as expected !!

Does anyone have an idea?

In any case whether outlook.com needs special preparation or setting changes or ms changed behaviour of mail server.
But what is clear now is that description here about outlook.com/hotmail.com seems to be wrong meanwhile!

  • Expected behavior: Provider works out of the box
  • Actual behavior: As soon as encryption is activated - see issue description

Does anyone have experience with ?

@r10s

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commented Mar 3, 2019

unfortunately, outlook and hotmail seems to have a whitelist for outgoing headers - and the Autocrypt: header as well as the Chat-Version and related headers are not part of this whitelist currently.

@adbenitez

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commented Mar 3, 2019

@r10s

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commented Mar 3, 2019

i think we can work around this in a way, however, seems as if no one had the time yet :)

@csb0730

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commented Mar 5, 2019

In a first step this should be documented in provider list.

So DC users can find this information quickly. Especially new users should get aware of this provider issue as quick as possible!
They immediately assume a problem of DC itself if running into this situation.

@Vistaus

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commented Apr 19, 2019

Does not work indeed. Messages are sent and arrive in the Inbox, but are not displayed in the Delta Chat app.

@Vistaus

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commented May 14, 2019

Any updates? Would love to use my Outlook account in Delta.

@r10s

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commented May 14, 2019

Any updates? Would love to use my Outlook account in Delta.

afaik, not yet from the Delta Chat side. however, maybe Microsoft has stopped stripping outgoing Autocrypt- or Chat-*-Headers meanwhile ;)

@csb0730

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commented May 16, 2019

My experience in the past was: As long as encryption is switched off, dc is working with outlook.com.

Make a trial. See dc's settings to switch off encryption.

@csb0730

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commented May 16, 2019

An unusual approach to get outlook.com working would be to move the autocrypt staff into mail body!?

Extending Autocrypt standard by this fallback?

@hpk42

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commented May 16, 2019

@csb0730

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commented May 23, 2019

I mean, a standard pgp encrypted message does the same in putting all pgp encrypted stuff into the mail body. Why autocrypt (or dc) cannot use the same approach?
Anyway: If we have an encrypted mail by autocrypt why not include the public key in body too?
Maybe this could be forced by a special user setting?

@r10s

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commented May 23, 2019

I mean, a standard pgp encrypted message does the same in putting all pgp encrypted stuff into the mail body.
Why autocrypt (or dc) cannot use the same approach?
Anyway: If we have an encrypted mail by autocrypt why not include the public key in body too?

this - and more - is answered in the autocrypt-faq: https://autocrypt.org/faq.html#why-are-you-using-headers-rather-than-attached-keys

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