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 <[email protected]> 
> 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 <[email protected]> 
>>>> 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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