Yeah this was unrelated to opensmtpd, everything works great when using mutt.

> On Sep 13, 2022, at 11:50, Ethan Ongstad <eongs...@icloud.com> wrote:
> 
> Oh jeez I typed it in wrong twice… Thanks for looking into this. I am using 
> the Mail command that ships with OpenBSD so I guess that is where my issue 
> lies.
> 
>> On Sep 13, 2022, at 11:00, Tassilo Philipp <tphil...@potion-studios.com> 
>> wrote:
>> 
>> 3): or it's the side that composes the mail that writes bad mail headers
>> 
>> 
>> On Tue, Sep 13, 2022 at 07:58:48PM +0200, Tassilo Philipp wrote:
>>> Well:
>>> 
>>> 1) if it's really 'Content-Type: Type: text/plain; charset=“utf-8”', it's 
>>> also wrong, the other "Type:" shouldn't be there, and the quotes (") aren't 
>>> ascii 0x22h quotes, but unicode ones (the quote thing is probably the 
>>> result of your client fancying things up pointlessly or copy and paste or 
>>> dunno...)
>>> 
>>> 2) none of this should have to do anything with OpenSMTPd, it's not parsing 
>>> your mails and trying to make sense of UTF-8 or so; this means if it's not 
>>> readable it's most likely your client not getting it right
>>> 
>>> hth
>>> 
>>> On Tue, Sep 13, 2022 at 10:08:18AM -0700, Ethan Ongstad wrote:
>>>> Nice catch. Actually that’s how it was in the message ( Content-Type: 
>>>> Type: text/plain; charset=“utf-8”  ). After looking at it again, the 
>>>> unreadable messages do have a base64 encoding, should this be an issue?
>>>> 
>>>>> On Sep 13, 2022, at 08:58, Tassilo Philipp <tphil...@potion-studios.com> 
>>>>> wrote:
>>>>> 
>>>>> not sure if related, but I noticed your line says "text:plain" instead of 
>>>>> "text/plain" (which should be used according to rfc2045)
>>>>> 
>>>>> 
>>>>> On Mon, Sep 12, 2022 at 10:20:38PM -0700, Ethan Ongstad wrote:
>>>>>> The messages I receive that have the line ‘ Content-Type: text:plain; 
>>>>>> charset="utf-8” ‘ are not readable, but it is human readable if the 
>>>>>> "utf-8" bit is capitalized or if there are no quotation marks. Is this a 
>>>>>> opensmtpd bug?
>>>>>> 
>>>>>> section 2 of RFC 2047 makes it sound like capitalization should not be 
>>>>>> relevant. https://www.rfc-editor.org/rfc/rfc2047#section-2 
>>>>>> <https://www.rfc-editor.org/rfc/rfc2047#section-2>
>>>>> 
>>>> 
>> 
> 
> 


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