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From: vaibhav singh <vaibhavsinghacads@gmail.com>
Date: Mon, 13 Nov 2017 20:40:03 +0530
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Subject: [imapext] General Request for Assignment (imap-keywords) (was: [JMAP] SMIME Attachments)
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--001a114c9d0c412f9f055ddeaabd
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Hello,

In order to optimize the way attachments inside encrypted mail are treated
by the MUA, I am suggesting the registration of a "$HasEncryptedAttachment"
to the IMAP Keywords registry[RFC5788].

Please find details of the original proposal below:

> Type of Assignment:
>  Requesting for addition of a keyword "$HasEncryptedAttachment" to the
> IMAP Keywords registry[RFC5788].
>
> Registry:
> The registration request is being made for IMAP Keywords
> registry[RFC5788].
>
> Description:
>     This flag can be useful so that the MUA can display an attachment
> icon when displaying
>    messages in the folder, without it having to decrypt the message.
> This flag can also be used to filter
>    encrypted emails with attachments.
>
> Additional Info:
>  The $HasEncryptedAttachment IMAP keyword will be used by IMAP/JMAP
> MUA to
>    specify that the marked encrypted message contains an attachment.
> A MUA-with-keys
>    sets this keyword when it sees a message having an attachment
> before encryption.
>     This flag can be useful so that the MUA can display an attachment
> icon when displaying
>    messages in the folder, without it having to decrypt the message.
> This flag can also be used to filter
>    encrypted emails with attachments.
>
> Once set, any entity (be it the MDA or receiver's MUA) SHOULD not edit
> the flag.
>
> JMAP Message Stores SHOULD be able to store the
> $HasEncryptedAttachment keyword.
> They MUST preserve it on the COPY operation.  The servers MUST
> support the SEARCH KEYWORD $HasEncryptedAttachment.

Please find comments by Mr. Barry Leiba, and my answers below (marked as
<vs>):

1.) There should also be a =E2=80=9Chas no attachment=E2=80=9D keyword, so =
the MUA doesn=E2=80=99t
have to check either way and only needs to check if neither is set.

 <vs>  Agreed. </vs>

2.) The keyword is poorly named: it=E2=80=99s not about an encrypted attach=
ment,
but about any attachment.  I suppose that in the end there no reason to
mention encryption at all, because it could be used for any message, though
it=E2=80=99s less important for unencrypted ones.

 <vs> Not really sure. </vs>

3.) How will the server know to set the keyword?  The server also can=E2=80=
=99t
decrypt an incoming message, and so it can=E2=80=99t check.  Where does the
knowledge come from?  It seems that it could only work for messages that
are created locally, with the keyword set at creation.

  <vs> A better use case for the flag could be: the server could set this
flag to true when it sees the mime being decrypted the first time, so that
any scans later on would not have to decrypt the mail again to know the
presence of the attachment inside it </vs>

Will this be useful?

--=20

Regards,
Vaibhav Singh

--001a114c9d0c412f9f055ddeaabd
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<div dir=3D"ltr"><div><div>Hello,<br><br></div>In order to optimize the way=
 attachments inside encrypted mail are treated by the MUA, I am suggesting =
the registration of a &quot;$HasEncryptedAttachment&quot; to the IMAP Keywo=
rds registry[RFC5788].<br></div><br>Please find details of the original pro=
posal below:<br><br clear=3D"all"><div>&gt; Type of Assignment:<br>&gt;=C2=
=A0 Requesting for addition of a keyword &quot;$HasEncryptedAttachment&quot=
; to the<br>&gt; IMAP Keywords registry[RFC5788].<br>&gt;<br>&gt; Registry:=
<br>&gt; The registration request is being made for IMAP Keywords<br>&gt; r=
egistry[RFC5788].<br>&gt;<br>&gt; Description:<br>&gt;=C2=A0 =C2=A0 =C2=A0T=
his flag can be useful so that the MUA can display an attachment<br>&gt; ic=
on when displaying<br>&gt;=C2=A0 =C2=A0 messages in the folder, without it =
having to decrypt the message.<br>&gt; This flag can also be used to filter=
<br>&gt;=C2=A0 =C2=A0 encrypted emails with attachments.<br>&gt;<br>&gt; Ad=
ditional Info:<br>&gt;=C2=A0 The $HasEncryptedAttachment IMAP keyword will =
be used by IMAP/JMAP<br>&gt; MUA to<br>&gt;=C2=A0 =C2=A0 specify that the m=
arked encrypted message contains an attachment.<br>&gt; A MUA-with-keys<br>=
&gt;=C2=A0 =C2=A0 sets this keyword when it sees a message having an attach=
ment<br>&gt; before encryption.<br>&gt;=C2=A0 =C2=A0 =C2=A0This flag can be=
 useful so that the MUA can display an attachment<br>&gt; icon when display=
ing<br>&gt;=C2=A0 =C2=A0 messages in the folder, without it having to decry=
pt the message.<br>&gt; This flag can also be used to filter<br>&gt;=C2=A0 =
=C2=A0 encrypted emails with attachments.<br>&gt;<br>&gt; Once set, any ent=
ity (be it the MDA or receiver&#39;s MUA) SHOULD not edit<br>&gt; the flag.=
<br>&gt;<br>&gt; JMAP Message Stores SHOULD be able to store the<br>&gt; $H=
asEncryptedAttachment keyword.<br>&gt; They MUST preserve it on the COPY op=
eration.=C2=A0 The servers MUST<br>&gt; support the SEARCH KEYWORD $HasEncr=
yptedAttachment.</div><div><br></div><div>Please find comments by Mr. Barry=
 Leiba, and my answers below (marked as &lt;vs&gt;):</div><div><br></div><d=
iv>1.) There should also be a =E2=80=9Chas no attachment=E2=80=9D keyword, =
so the MUA doesn=E2=80=99t have to check either way and only needs to check=
 if neither is set.</div><div>=C2=A0=C2=A0 <br></div><div>=C2=A0&lt;vs&gt;=
=C2=A0 Agreed. &lt;/vs&gt;</div><div><br></div><div>2.) The keyword is poor=
ly named: it=E2=80=99s not about an encrypted attachment, but about any att=
achment.=C2=A0 I suppose that in the end there no reason to mention encrypt=
ion at all, because it could be used for any message, though it=E2=80=99s l=
ess important for unencrypted ones. <br></div><div><br></div><div>=C2=A0&lt=
;vs&gt; Not really sure. &lt;/vs&gt;</div><div><br></div><div>3.) How will =
the server know to set the keyword?=C2=A0 The server also can=E2=80=99t dec=
rypt an incoming message, and so it can=E2=80=99t check.=C2=A0 Where does t=
he knowledge come from?=C2=A0 It seems that it could only work for messages=
 that are created locally, with the keyword set at creation.</div><div>=C2=
=A0</div><div>=C2=A0 &lt;vs&gt; A better use case for the flag could be: th=
e server could set this flag to true when it sees the mime being decrypted =
the first time, so that any scans later on would not have to decrypt the ma=
il again to know the presence of the attachment inside it &lt;/vs&gt;</div>=
<div><br></div>Will this be useful?<br clear=3D"all"><br>-- <br><div class=
=3D"gmail_signature"><div dir=3D"ltr"><div><br></div>Regards,<div>Vaibhav S=
ingh</div></div></div>
</div>

--001a114c9d0c412f9f055ddeaabd--


From nobody Tue Nov 14 00:25:33 2017
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From: Arnt Gulbrandsen <arnt@gulbrandsen.priv.no>
To: vaibhav singh <vaibhavsinghacads@gmail.com>
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Date: Tue, 14 Nov 2017 08:25:23 +0000
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Subject: Re: [imapext] General Request for Assignment (imap-keywords) (was: [JMAP] SMIME Attachments)
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Hi,

sorry about the late response. I suck at the moment.

I don't understand the semantics here.

If present, it means that someone has checked and found an encrypted 
attachment. And if absent, it means nothing. There may or may not be an 
encrypted attachment.

So my question is, what advantage does this provide over checking the 
bodystructure?

Arnt


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Date: Wed, 15 Nov 2017 01:06:58 +1100
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Subject: Re: [imapext] General Request for Assignment (imap-keywords) (was: [JMAP] SMIME Attachments)
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On Tue, 14 Nov 2017, at 19:25, Arnt Gulbrandsen wrote:
> Hi,
> 
> sorry about the late response. I suck at the moment.
> 
> I don't understand the semantics here.
> 
> If present, it means that someone has checked and found an encrypted
> attachment. And if absent, it means nothing. There may or may
> not be an> encrypted attachment.
> 
> So my question is, what advantage does this provide over checking the> bodystructure?

The usecase is that the entire message is encrypted as a single blob,
but it contains an attachment.  The client wants to mark that so that
other clients know it has an attachment.
There are questions about that being a metadata leak that haven't been
addressed.
There are questions that Barry and I spoke about briefly on Saturday
about pairing it with a $HasNoEncryptedAttachment or something so you
can tell that it's been checked already, which led to a general
discussion about paired keywords and what it means if they're both set
and wouldn't it be nice if we had tristate keywords and what about per-message-
annotations and doesn't everything suck.
But yeah, I'm pretty sure the intention was just that clients would use
it to communicate to each other something about the content of the
message inside the related opaque blob that is the message, in a case
where a user has multiple clients that all know how to decrypt the
message, but the server doesn't.
I have no idea where that most  idea of the server setting the flag in
Vaibhav's most recent email came from - the whole point in the original
scenario is that the server doesn't know anything about the content of
the email.
Anyway, I don't think the whole way this would work has been well
thought out yet.
Bron.

--
  Bron Gondwana, CEO, FastMail Pty Ltd
  brong@fastmailteam.com



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<div>On Tue, 14 Nov 2017, at 19:25, Arnt Gulbrandsen wrote:<br></div>
<blockquote type="cite"><div>Hi,<br></div>
<div><br></div>
<div>sorry about the late response. I suck at the moment.<br></div>
<div><br></div>
<div>I don't understand the semantics here.<br></div>
<div><br></div>
<div>If present, it means that someone has checked and found an encrypted<br></div>
<div>attachment. And if absent, it means nothing. There may or may not be an<br></div>
<div>encrypted attachment.<br></div>
<div><br></div>
<div>So my question is, what advantage does this provide over checking the<br></div>
<div>bodystructure?<br></div>
</blockquote><div><br></div>
<div style="font-family:Arial;">The usecase is that the entire message is encrypted as a single blob, but it contains an attachment.&nbsp; The client wants to mark that so that other clients know it has an attachment.<br></div>
<div style="font-family:Arial;"><br>There are questions about that being a metadata leak that haven't been addressed.</div>
<div style="font-family:Arial;"><br></div>
<div style="font-family:Arial;">There are questions that Barry and I spoke about briefly on Saturday about pairing it with a $HasNoEncryptedAttachment or something so you can tell that it's been checked already, which led to a general discussion about paired keywords and what it means if they're both set and wouldn't it be nice if we had tristate keywords and what about per-message-annotations and doesn't everything suck.<br></div>
<div style="font-family:Arial;"><br></div>
<div style="font-family:Arial;">But yeah, I'm pretty sure the intention was just that clients would use it to communicate to each other something about the content of the message inside the related opaque blob that is the message, in a case where a user has multiple clients that all know how to decrypt the message, but the server doesn't.<br></div>
<div style="font-family:Arial;"><br></div>
<div style="font-family:Arial;">I have no idea where that most  idea of the server setting the flag in Vaibhav's most recent email came from - the whole point in the original scenario is that the server doesn't know anything about the content of the email.<br></div>
<div style="font-family:Arial;"><br></div>
<div style="font-family:Arial;">Anyway, I don't think the whole way this would work has been well thought out yet.<br></div>
<div style="font-family:Arial;"><br></div>
<div style="font-family:Arial;">Bron.<br></div>
<div style="font-family:Arial;"><br></div>
<div style="font-family:Arial;">--<br></div>
<div id="sig56629417"><div class="signature">&nbsp; Bron Gondwana, CEO, FastMail Pty Ltd<br></div>
<div class="signature">&nbsp; brong@fastmailteam.com<br></div>
<div class="signature"><br></div>
</div>
<div style="font-family:Arial;"><br></div>
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From: Arnt Gulbrandsen <arnt@gulbrandsen.priv.no>
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Date: Tue, 14 Nov 2017 14:25:06 +0000
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Subject: Re: [imapext] General Request for Assignment (imap-keywords) (was: [JMAP] SMIME Attachments)
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Bron Gondwana writes:
> The usecase is that the entire message is encrypted as a single 
> blob, but it contains an attachment.  The client wants to mark 
> that so that other clients know it has an attachment.

Oh, right.

> There are questions about that being a metadata leak that 
> haven't been addressed.

I thought about those and it seems insignificant. The size of the encrypted 
blob is a good proxy for that information anyway. Big? Attachment. Small? 
No.

> Anyway, I don't think the whole way this would work has been 
> well thought out yet.

AOL. It would seem to serve the case where the user uses two clients, both 
of which display whether a message has an attachment and neither of which 
displays any other information from inside the blob. In particular, neither 
can display an excerpt of the text, or any information about the kind of 
attachment.

Arnt


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Date: Tue, 14 Nov 2017 09:58:42 -0500
From: Cyrus Daboo <cyrus@daboo.name>
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Hi Arnt,

--On November 14, 2017 at 2:25:06 PM +0000 Arnt Gulbrandsen 
<arnt@gulbrandsen.priv.no> wrote:

>> Anyway, I don't think the whole way this would work has been
>> well thought out yet.
>
> AOL. It would seem to serve the case where the user uses two clients,
> both of which display whether a message has an attachment and neither of
> which displays any other information from inside the blob. In particular,
> neither can display an excerpt of the text, or any information about the
> kind of attachment.
>

I think a much more useful option would be for the first client to decrypt 
the blob and generate an IMAP-like BODYSTRUCTURE which it then encrypts to 
the user's public key and uploads as metadata attached to the original 
message. Then other clients which have the private key can grab the 
metadata and decrypt it to get the full structure of the encrypted blob. 
That way the clients get to learn a lot more about the message than the 
mere fact it contains an attachment.

Note, that it might also be useful to send the encrypted BODYSTRUCTURE data 
as a separate part/header in the encrypted message. That way recipients 
would also gain the benefit of being able to quickly determine what the 
message contains. Of course that additional data does potentially leak some 
information about the message, but that might be acceptable.

-- 
Cyrus Daboo


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Subject: Re: [imapext] General Request for Assignment (imap-keywords) (was: [JMAP] SMIME Attachments)
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On Wed, 15 Nov 2017, at 01:58, Cyrus Daboo wrote:
> Hi Arnt,
> 
> --On November 14, 2017 at 2:25:06 PM +0000 Arnt Gulbrandsen
> <arnt@gulbrandsen.priv.no> wrote:
> 
>>> Anyway, I don't think the whole way this would work has been
>>> well thought out yet.
>> 
>> AOL. It would seem to serve the case where the user uses two clients,>> both of which display whether a message has an attachment and
>> neither of>> which displays any other information from inside the blob. In
>> particular,>> neither can display an excerpt of the text, or any information
>> about the>> kind of attachment.
>> 
> 
> I think a much more useful option would be for the first client to
> decrypt
> the blob and generate an IMAP-like BODYSTRUCTURE which it then
> encrypts> to
> the user's public key and uploads as metadata attached to the original> message. Then other clients which have the private key can grab the
> metadata and decrypt it to get the full structure of the
> encrypted blob.> That way the clients get to learn a lot more about the message
> than the> mere fact it contains an attachment.
> 
> Note, that it might also be useful to send the encrypted BODYSTRUCTURE> data
> as a separate part/header in the encrypted message. That way
> recipients> would also gain the benefit of being able to quickly determine
> what the> message contains. Of course that additional data does potentially leak> some
> information about the message, but that might be acceptable.

The main value of any non-encrypted facts about the message (like a
keyword about the attachment state) is to allow server-side search.
I agree with Cyrus - the sender could easily attach the BODYSTRUCTURE as
a separate encrypted part, though again that leaks information about the
structure based on the size of the encrypted part - all sorts of side
channel/metadata stuff needs to be thought through, and different people
have different tradeoffs/risk profiles - but then most people don't want
to think that deeply about every message they send, so if you make it
too complex nobody will use it.
Regardless of what gets stored encrypted or who does it however, the
value of a keyword is search/sort.
I still remain unconvinced that the usecase is common enough that any
client would use it, particularly since the first client still needs to
download the message so it can set the flag.
Bron.

--
  Bron Gondwana, CEO, FastMail Pty Ltd
  brong@fastmailteam.com



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<body><div style="font-family:Arial;">On Wed, 15 Nov 2017, at 01:58, Cyrus Daboo wrote:<br></div>
<blockquote type="cite"><div>Hi Arnt,<br></div>
<div><br></div>
<div>--On November 14, 2017 at 2:25:06 PM +0000 Arnt Gulbrandsen<br></div>
<div>&lt;<a href="mailto:arnt@gulbrandsen.priv.no">arnt@gulbrandsen.priv.no</a>&gt; wrote:<br></div>
<div><br></div>
<blockquote><blockquote><div>Anyway, I don't think the whole way this would work has been<br></div>
<div>well thought out yet.<br></div>
</blockquote><div><br></div>
<div>AOL. It would seem to serve the case where the user uses two clients,<br></div>
<div>both of which display whether a message has an attachment and neither of<br></div>
<div>which displays any other information from inside the blob. In particular,<br></div>
<div>neither can display an excerpt of the text, or any information about the<br></div>
<div>kind of attachment.<br></div>
<div><br></div>
</blockquote><div><br></div>
<div>I think a much more useful option would be for the first client to<br></div>
<div>decrypt<br></div>
<div>the blob and generate an IMAP-like BODYSTRUCTURE which it then encrypts<br></div>
<div>to<br></div>
<div>the user's public key and uploads as metadata attached to the original<br></div>
<div>message. Then other clients which have the private key can grab the<br></div>
<div>metadata and decrypt it to get the full structure of the encrypted blob.<br></div>
<div>That way the clients get to learn a lot more about the message than the<br></div>
<div>mere fact it contains an attachment.<br></div>
<div><br></div>
<div>Note, that it might also be useful to send the encrypted BODYSTRUCTURE<br></div>
<div>data<br></div>
<div>as a separate part/header in the encrypted message. That way recipients<br></div>
<div>would also gain the benefit of being able to quickly determine what the<br></div>
<div>message contains. Of course that additional data does potentially leak<br></div>
<div>some<br></div>
<div>information about the message, but that might be acceptable.<br></div>
</blockquote><div style="font-family:Arial;"><br></div>
<div style="font-family:Arial;">The main value of any non-encrypted facts about the message (like a keyword about the attachment state) is to allow server-side search.<br></div>
<div style="font-family:Arial;"><br></div>
<div style="font-family:Arial;">I agree with Cyrus - the sender could easily attach the BODYSTRUCTURE as a separate encrypted part, though again that leaks information about the structure based on the size of the encrypted part - all sorts of side channel/metadata stuff needs to be thought through, and different people have different tradeoffs/risk profiles - but then most people don't want to think that deeply about every message they send, so if you make it too complex nobody will use it.<br></div>
<div style="font-family:Arial;"><br></div>
<div style="font-family:Arial;">Regardless of what gets stored encrypted or who does it however, the value of a keyword is search/sort.<br></div>
<div style="font-family:Arial;"><br></div>
<div style="font-family:Arial;">I still remain unconvinced that the usecase is common enough that any client would use it, particularly since the first client still needs to download the message so it can set the flag.<br></div>
<div style="font-family:Arial;"><br>Bron.<br></div>
<div style="font-family:Arial;"><br></div>
<div id="sig56629417"><div class="signature">--<br></div>
<div class="signature">&nbsp; Bron Gondwana, CEO, FastMail Pty Ltd<br></div>
<div class="signature">&nbsp; brong@fastmailteam.com<br></div>
<div class="signature"><br></div>
</div>
<div style="font-family:Arial;"><br></div>
</body>
</html>

--_----------=_151070507017805990--


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From: Barry Leiba <barryleiba@computer.org>
Date: Wed, 15 Nov 2017 10:43:25 +0800
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To: vaibhav singh <vaibhavsinghacads@gmail.com>
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Subject: Re: [imapext] General Request for Assignment (imap-keywords) (was: [JMAP] SMIME Attachments)
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Vaibhav left off one significant bit of my review:

4.  ...the term =E2=80=9Cattachment=E2=80=9D is a bit odd in today=E2=80=99=
s usage.  Messages
may have multiple parts.  Whether some or all of those parts appear to
the user as =E2=80=9Cattachments=E2=80=9D depends upon the rendering.  For =
example, a
two-part message that is multipart/alternative... is there an
=E2=80=9Cattachment=E2=80=9D?  How about a single-part message that is imag=
e/jpeg,
with no text at all?  What about if I forward a message and the
forwarded message is included as a separate message/rfc822 part rather
than being included in the main text?

Barry


On Mon, Nov 13, 2017 at 11:10 PM, vaibhav singh
<vaibhavsinghacads@gmail.com> wrote:
> Hello,
>
> In order to optimize the way attachments inside encrypted mail are treate=
d
> by the MUA, I am suggesting the registration of a "$HasEncryptedAttachmen=
t"
> to the IMAP Keywords registry[RFC5788].
>
> Please find details of the original proposal below:
>
>> Type of Assignment:
>>  Requesting for addition of a keyword "$HasEncryptedAttachment" to the
>> IMAP Keywords registry[RFC5788].
>>
>> Registry:
>> The registration request is being made for IMAP Keywords
>> registry[RFC5788].
>>
>> Description:
>>     This flag can be useful so that the MUA can display an attachment
>> icon when displaying
>>    messages in the folder, without it having to decrypt the message.
>> This flag can also be used to filter
>>    encrypted emails with attachments.
>>
>> Additional Info:
>>  The $HasEncryptedAttachment IMAP keyword will be used by IMAP/JMAP
>> MUA to
>>    specify that the marked encrypted message contains an attachment.
>> A MUA-with-keys
>>    sets this keyword when it sees a message having an attachment
>> before encryption.
>>     This flag can be useful so that the MUA can display an attachment
>> icon when displaying
>>    messages in the folder, without it having to decrypt the message.
>> This flag can also be used to filter
>>    encrypted emails with attachments.
>>
>> Once set, any entity (be it the MDA or receiver's MUA) SHOULD not edit
>> the flag.
>>
>> JMAP Message Stores SHOULD be able to store the
>> $HasEncryptedAttachment keyword.
>> They MUST preserve it on the COPY operation.  The servers MUST
>> support the SEARCH KEYWORD $HasEncryptedAttachment.
>
> Please find comments by Mr. Barry Leiba, and my answers below (marked as
> <vs>):
>
> 1.) There should also be a =E2=80=9Chas no attachment=E2=80=9D keyword, s=
o the MUA doesn=E2=80=99t
> have to check either way and only needs to check if neither is set.
>
>  <vs>  Agreed. </vs>
>
> 2.) The keyword is poorly named: it=E2=80=99s not about an encrypted atta=
chment, but
> about any attachment.  I suppose that in the end there no reason to menti=
on
> encryption at all, because it could be used for any message, though it=E2=
=80=99s
> less important for unencrypted ones.
>
>  <vs> Not really sure. </vs>
>
> 3.) How will the server know to set the keyword?  The server also can=E2=
=80=99t
> decrypt an incoming message, and so it can=E2=80=99t check.  Where does t=
he
> knowledge come from?  It seems that it could only work for messages that =
are
> created locally, with the keyword set at creation.
>
>   <vs> A better use case for the flag could be: the server could set this
> flag to true when it sees the mime being decrypted the first time, so tha=
t
> any scans later on would not have to decrypt the mail again to know the
> presence of the attachment inside it </vs>
>
> Will this be useful?
>
> --
>
> Regards,
> Vaibhav Singh
>
> _______________________________________________
> imapext mailing list
> imapext@ietf.org
> https://www.ietf.org/mailman/listinfo/imapext
>


From nobody Tue Nov 14 18:55:21 2017
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From: Alexey Melnikov <alexey.melnikov@isode.com>
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Subject: Re: [imapext] General Request for Assignment (imap-keywords) (was: [JMAP] SMIME Attachments)
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On 15/11/2017 10:43, Barry Leiba wrote:
> Vaibhav left off one significant bit of my review:
>=20
> 4.  ...the term =E2=80=9Cattachment=E2=80=9D is a bit odd in today=E2=80=
=99s usage.  Messages
> may have multiple parts.  Whether some or all of those parts appear to
> the user as =E2=80=9Cattachments=E2=80=9D depends upon the rendering.  For=
 example, a
> two-part message that is multipart/alternative... is there an
> =E2=80=9Cattachment=E2=80=9D?  How about a single-part message that is ima=
ge/jpeg,
> with no text at all?  What about if I forward a message and the
> forwarded message is included as a separate message/rfc822 part rather
> than being included in the main text?

I think "Content-Disposition: attachment" is a good indicator of whether
something is an "attachment". In absence of Content-Disposition any
decision is an heuristic.

> Barry
>=20
>=20
> On Mon, Nov 13, 2017 at 11:10 PM, vaibhav singh
> <vaibhavsinghacads@gmail.com> wrote:
>> Hello,
>>
>> In order to optimize the way attachments inside encrypted mail are treate=
d
>> by the MUA, I am suggesting the registration of a "$HasEncryptedAttachmen=
t"
>> to the IMAP Keywords registry[RFC5788].
>>
>> Please find details of the original proposal below:
>>
>>> Type of Assignment:
>>>  Requesting for addition of a keyword "$HasEncryptedAttachment" to the
>>> IMAP Keywords registry[RFC5788].
>>>
>>> Registry:
>>> The registration request is being made for IMAP Keywords
>>> registry[RFC5788].
>>>
>>> Description:
>>>     This flag can be useful so that the MUA can display an attachment
>>> icon when displaying
>>>    messages in the folder, without it having to decrypt the message.
>>> This flag can also be used to filter
>>>    encrypted emails with attachments.
>>>
>>> Additional Info:
>>>  The $HasEncryptedAttachment IMAP keyword will be used by IMAP/JMAP
>>> MUA to
>>>    specify that the marked encrypted message contains an attachment.
>>> A MUA-with-keys
>>>    sets this keyword when it sees a message having an attachment
>>> before encryption.
>>>     This flag can be useful so that the MUA can display an attachment
>>> icon when displaying
>>>    messages in the folder, without it having to decrypt the message.
>>> This flag can also be used to filter
>>>    encrypted emails with attachments.
>>>
>>> Once set, any entity (be it the MDA or receiver's MUA) SHOULD not edit
>>> the flag.
>>>
>>> JMAP Message Stores SHOULD be able to store the
>>> $HasEncryptedAttachment keyword.
>>> They MUST preserve it on the COPY operation.  The servers MUST
>>> support the SEARCH KEYWORD $HasEncryptedAttachment.
>>
>> Please find comments by Mr. Barry Leiba, and my answers below (marked as
>> <vs>):
>>
>> 1.) There should also be a =E2=80=9Chas no attachment=E2=80=9D keyword, s=
o the MUA doesn=E2=80=99t
>> have to check either way and only needs to check if neither is set.
>>
>>  <vs>  Agreed. </vs>
>>
>> 2.) The keyword is poorly named: it=E2=80=99s not about an encrypted atta=
chment, but
>> about any attachment.  I suppose that in the end there no reason to menti=
on
>> encryption at all, because it could be used for any message, though it=E2=
=80=99s
>> less important for unencrypted ones.
>>
>>  <vs> Not really sure. </vs>
>>
>> 3.) How will the server know to set the keyword?  The server also can=E2=
=80=99t
>> decrypt an incoming message, and so it can=E2=80=99t check.  Where does t=
he
>> knowledge come from?  It seems that it could only work for messages that =
are
>> created locally, with the keyword set at creation.
>>
>>   <vs> A better use case for the flag could be: the server could set this
>> flag to true when it sees the mime being decrypted the first time, so tha=
t
>> any scans later on would not have to decrypt the mail again to know the
>> presence of the attachment inside it </vs>
>>
>> Will this be useful?
>>
>> --
>>
>> Regards,
>> Vaibhav Singh
>>
>> _______________________________________________
>> imapext mailing list
>> imapext@ietf.org
>> https://www.ietf.org/mailman/listinfo/imapext
>>
>=20
> _______________________________________________
> imapext mailing list
> imapext@ietf.org
> https://www.ietf.org/mailman/listinfo/imapext
>=20


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Subject: Re: [imapext] General Request for Assignment (imap-keywords) (was: [JMAP] SMIME Attachments)
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>> 4.  ...the term =E2=80=9Cattachment=E2=80=9D is a bit odd in today=E2=80=
=99s usage.  Messages
>> may have multiple parts.  Whether some or all of those parts appear to
>> the user as =E2=80=9Cattachments=E2=80=9D depends upon the rendering.  F=
or example, a
>> two-part message that is multipart/alternative... is there an
>> =E2=80=9Cattachment=E2=80=9D?  How about a single-part message that is i=
mage/jpeg,
>> with no text at all?  What about if I forward a message and the
>> forwarded message is included as a separate message/rfc822 part rather
>> than being included in the main text?
>
> I think "Content-Disposition: attachment" is a good indicator of whether
> something is an "attachment". In absence of Content-Disposition any
> decision is an heuristic.

Sure, but the use of Content-Disposition is sporadic and unreliable.

I think that, basically, this issue speaks to a preference for the
suggestion of storing a BODYPART parse on first use, and then being
able to use that for optimization later.

Barry


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--f403045fc07cffb2a9055e11e651
Content-Type: text/plain; charset="UTF-8"

> ---------- Forwarded message ----------
> From: Bron Gondwana <brong@fastmailteam.com>
> To: imapext@ietf.org
> Cc:
> Bcc:
> Date: Wed, 15 Nov 2017 01:06:58 +1100
> Subject: Re: [imapext] General Request for Assignment (imap-keywords)
> (was: [JMAP] SMIME Attachments)
>
> On Tue, 14 Nov 2017, at 19:25, Arnt Gulbrandsen wrote:
>
> Hi,
>
> sorry about the late response. I suck at the moment.
>
> I don't understand the semantics here.
>
> If present, it means that someone has checked and found an encrypted
> attachment. And if absent, it means nothing. There may or may not be an
> encrypted attachment.
>
> So my question is, what advantage does this provide over checking the
> bodystructure?
>
>
> The usecase is that the entire message is encrypted as a single blob, but
> it contains an attachment.  The client wants to mark that so that other
> clients know it has an attachment.
>
> There are questions about that being a metadata leak that haven't been
> addressed.
>
> There are questions that Barry and I spoke about briefly on Saturday about
> pairing it with a $HasNoEncryptedAttachment or something so you can tell
> that it's been checked already, which led to a general discussion about
> paired keywords and what it means if they're both set and wouldn't it be
> nice if we had tristate keywords and what about per-message-annotations and
> doesn't everything suck.
>
> But yeah, I'm pretty sure the intention was just that clients would use it
> to communicate to each other something about the content of the message
> inside the related opaque blob that is the message, in a case where a user
> has multiple clients that all know how to decrypt the message, but the
> server doesn't.
>
> I have no idea where that most idea of the server setting the flag in
> Vaibhav's most recent email came from - the whole point in the original
> scenario is that the server doesn't know anything about the content of the
> email.
>
> Sorry if there has been some miscommunication from my side, of the server
being the entity setting the flag. The flag will be set by the party having
access to the decryption keys (almost always the MUA), but this information
will be stored as part of the message meta information, intermediated by
the server.

Thanks,
Vaibhav

Anyway, I don't think the whole way this would work has been well thought
> out yet.
>
> Bron.
>
> --
>   Bron Gondwana, CEO, FastMail Pty Ltd
>   brong@fastmailteam.com
>
>
>
>
Regards,
Vaibhav Singh

--f403045fc07cffb2a9055e11e651
Content-Type: text/html; charset="UTF-8"
Content-Transfer-Encoding: quoted-printable

<div dir=3D"ltr"><br><div class=3D"gmail_extra"><br><div class=3D"gmail_quo=
te"><br><blockquote class=3D"gmail_quote" style=3D"margin:0 0 0 .8ex;border=
-left:1px #ccc solid;padding-left:1ex"><br>---------- Forwarded message ---=
-------<br>From:=C2=A0Bron Gondwana &lt;<a href=3D"mailto:brong@fastmailtea=
m.com">brong@fastmailteam.com</a>&gt;<br>To:=C2=A0<a href=3D"mailto:imapext=
@ietf.org">imapext@ietf.org</a><br>Cc:=C2=A0<br>Bcc:=C2=A0<br>Date:=C2=A0We=
d, 15 Nov 2017 01:06:58 +1100<br>Subject:=C2=A0Re: [imapext] General Reques=
t for Assignment (imap-keywords) (was: [JMAP] SMIME Attachments)<br><u></u>




<div><div style=3D"font-family:Arial"><br></div>
<div>On Tue, 14 Nov 2017, at 19:25, Arnt Gulbrandsen wrote:<br></div>
<blockquote type=3D"cite"><div>Hi,<br></div>
<div><br></div>
<div>sorry about the late response. I suck at the moment.<br></div>
<div><br></div>
<div>I don&#39;t understand the semantics here.<br></div>
<div><br></div>
<div>If present, it means that someone has checked and found an encrypted<b=
r></div>
<div>attachment. And if absent, it means nothing. There may or may not be a=
n<br></div>
<div>encrypted attachment.<br></div>
<div><br></div>
<div>So my question is, what advantage does this provide over checking the<=
br></div>
<div>bodystructure?<br></div>
</blockquote><div><br></div>
<div style=3D"font-family:Arial">The usecase is that the entire message is =
encrypted as a single blob, but it contains an attachment.=C2=A0 The client=
 wants to mark that so that other clients know it has an attachment.<br></d=
iv>
<div style=3D"font-family:Arial"><br>There are questions about that being a=
 metadata leak that haven&#39;t been addressed.</div>
<div style=3D"font-family:Arial"><br></div>
<div style=3D"font-family:Arial">There are questions that Barry and I spoke=
 about briefly on Saturday about pairing it with a $HasNoEncryptedAttachmen=
t or something so you can tell that it&#39;s been checked already, which le=
d to a general discussion about paired keywords and what it means if they&#=
39;re both set and wouldn&#39;t it be nice if we had tristate keywords and =
what about per-message-annotations and doesn&#39;t everything suck.<br></di=
v>
<div style=3D"font-family:Arial"><br></div>
<div style=3D"font-family:Arial">But yeah, I&#39;m pretty sure the intentio=
n was just that clients would use it to communicate to each other something=
 about the content of the message inside the related opaque blob that is th=
e message, in a case where a user has multiple clients that all know how to=
 decrypt the message, but the server doesn&#39;t.<br></div>
<div style=3D"font-family:Arial"><br></div>
<div style=3D"font-family:Arial">I have no idea where that most  idea of th=
e server setting the flag in Vaibhav&#39;s most recent email came from - th=
e whole point in the original scenario is that the server doesn&#39;t know =
anything about the content of the email.<br></div>
<div style=3D"font-family:Arial"><br></div></div></blockquote><div>Sorry if=
 there has been some miscommunication from my side, of the server being the=
 entity setting the flag. The flag will be set by the party having access t=
o the decryption keys (almost always the MUA), but this information will be=
 stored as part of the message meta information, intermediated by the serve=
r.</div><div><br></div><div>Thanks,</div><div>Vaibhav<br></div><div> <br></=
div><blockquote class=3D"gmail_quote" style=3D"margin:0 0 0 .8ex;border-lef=
t:1px #ccc solid;padding-left:1ex"><div><div style=3D"font-family:Arial"></=
div>
<div style=3D"font-family:Arial">Anyway, I don&#39;t think the whole way th=
is would work has been well thought out yet.<br></div>
<div style=3D"font-family:Arial"><br></div>
<div style=3D"font-family:Arial">Bron.<br></div>
<div style=3D"font-family:Arial"><br></div>
<div style=3D"font-family:Arial">--<br></div>
<div id=3D"m_5742012608132063126sig56629417"><div class=3D"m_57420126081320=
63126signature">=C2=A0 Bron Gondwana, CEO, FastMail Pty Ltd<br></div>
<div class=3D"m_5742012608132063126signature">=C2=A0 <a href=3D"mailto:bron=
g@fastmailteam.com" target=3D"_blank">brong@fastmailteam.com</a><br></div>
<div class=3D"m_5742012608132063126signature"><br></div>
</div>
<div style=3D"font-family:Arial"><br></div>
</div>

<br></blockquote></div><div class=3D"gmail_signature" data-smartmail=3D"gma=
il_signature"><div dir=3D"ltr"><div><br></div>Regards,<div>Vaibhav Singh</d=
iv></div></div>
</div></div>

--f403045fc07cffb2a9055e11e651--


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From: Neil Jhaveri <neil@neiljhaveri.com>
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To: Bron Gondwana <brong@fastmailteam.com>
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Subject: Re: [imapext] General Request for Assignment (imap-keywords) (was: [JMAP] SMIME Attachments)
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--Apple-Mail=_613F6718-30F4-4096-AEE3-686D87B87FA8
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> On Nov 14, 2017, at 5:17 PM, Bron Gondwana <brong@fastmailteam.com> =
wrote:
>=20
> I still remain unconvinced that the usecase is common enough that any =
client would use it, particularly since the first client still needs to =
download the message so it can set the flag.

I agree, I just don=E2=80=99t see the value of this being significant =
enough, since it only helps the second+ client that comes along.

If you are dealing with messages encrypted as a single blob, and want to =
have a good user experience, you probably have to venture into =
thick-client territory and proactively download/decrypt the message =
locally anyways. Otherwise, how can you provide full-text body search, =
or a UI with a message preview, as many clients seem to be doing =
nowadays?

Doesn=E2=80=99t that also diminish the need for this keyword?

Have I missed some important use-case?=

--Apple-Mail=_613F6718-30F4-4096-AEE3-686D87B87FA8
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<html><head><meta http-equiv=3D"Content-Type" content=3D"text/html =
charset=3Dutf-8"></head><body style=3D"word-wrap: break-word; =
-webkit-nbsp-mode: space; -webkit-line-break: after-white-space;" =
class=3D""><br class=3D""><div><blockquote type=3D"cite" class=3D""><div =
class=3D"">On Nov 14, 2017, at 5:17 PM, Bron Gondwana &lt;<a =
href=3D"mailto:brong@fastmailteam.com" =
class=3D"">brong@fastmailteam.com</a>&gt; wrote:</div><br =
class=3D"Apple-interchange-newline"><div class=3D""><span =
style=3D"font-family: Arial; font-size: 12px; font-style: normal; =
font-variant-caps: normal; font-weight: normal; letter-spacing: normal; =
text-align: start; text-indent: 0px; text-transform: none; white-space: =
normal; word-spacing: 0px; -webkit-text-stroke-width: 0px; float: none; =
display: inline !important;" class=3D"">I still remain unconvinced that =
the usecase is common enough that any client would use it, particularly =
since the first client still needs to download the message so it can set =
the flag.</span></div></blockquote></div><br class=3D""><div class=3D"">I =
agree, I just don=E2=80=99t see the value of this being significant =
enough, since it only helps the second+ client that comes =
along.</div><div class=3D""><br class=3D""></div><div class=3D"">If you =
are dealing with messages encrypted as a single blob, and want to have a =
good user experience, you probably have to venture into thick-client =
territory and proactively download/decrypt the message locally anyways. =
Otherwise, how can you provide full-text body search, or a UI with a =
message preview, as many clients seem to be doing nowadays?</div><div =
class=3D""><br class=3D""></div><div class=3D"">Doesn=E2=80=99t that =
also diminish the need for this keyword?</div><div class=3D""><br =
class=3D""></div><div class=3D"">Have I missed some important =
use-case?</div></body></html>=

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Subject: Re: [imapext] General Request for Assignment (imap-keywords) (was: [JMAP] SMIME Attachments)
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On 14 Nov 2017, at 8:06, Bron Gondwana wrote:
> On Tue, 14 Nov 2017, at 19:25, Arnt Gulbrandsen wrote:
>> Hi,
>>
>> sorry about the late response. I suck at the moment.
>>
>> I don't understand the semantics here.
>>
>> If present, it means that someone has checked and found an encrypted
>> attachment. And if absent, it means nothing. There may or may
>> not be an> encrypted attachment.
>>
>> So my question is, what advantage does this provide over checking 
>> the> bodystructure?
>
> The usecase is that the entire message is encrypted as a single blob,
> but it contains an attachment.  The client wants to mark that so that
> other clients know it has an attachment.

Typically "has attachment" is a UI flag. For encrypted mail, the server 
can't provide that information so the client must if it's going to be 
provided. So clients wanting to present that UI flag have to parse 
encrypted messages.

> There are questions about that being a metadata leak that haven't been
> addressed.

It is a deliberate leak of metadata. The nice thing about a leak of 1 or 
2 bits of information is that the scope of the leak is largely 
understood. With an encrypted body structure, I'm more concerned about 
the scope of the information leak as it leaks non-obvious information.

> There are questions that Barry and I spoke about briefly on Saturday
> about pairing it with a $HasNoEncryptedAttachment or something so you
> can tell that it's been checked already, which led to a general
> discussion about paired keywords and what it means if they're both set
> and wouldn't it be nice if we had tristate keywords and what about 
> per-message-
> annotations and doesn't everything suck.

This problem can be addressed by changing the definition as follows:

$ClientSawAttachment => at least one client believes this message has an 
attachment.
$ClientSawNoAttachment => at least one client believes this message does 
not have an attachment.

If both are set, that now has a meaning (specifically that the end-user 
uses at least two different clients that have different opinions on what 
constitutes an attachment and whether the message has one :-).

Basic guidelines for "has an attachment" calculations are:
* Content-Disposition: attachment anywhere in the message means the 
message has an attachment.
* If all parts have Content-Disposition: inline, that means the message 
has no attachment.
For the following four guidelines, implementation-defined exceptions are 
permitted:
* If the client can usefully render all MIME parts in a single view (and 
none are explicitly labelled an attachment), there's probably no 
attachment.
* If there's a MIME part the client can't usefully render, there 
probably is an attachment.
* multipart/related tends to imply that MIME subtree has no attachment 
unless the top-level type of the multipart/related is one the client 
can't render.
* multipart/alternative tends to imply that MIME subtree has no 
attachment if at least one part is a text part the client can render.

This is clearly somewhat heuristic when Content-Disposition is missing, 
but if the keywords are defined as above, I don't see a problem with 
that.

I don't find this issue particularly important given how rarely 
encrypted email is used, but since there seems to be interest from more 
than one implementer, I don't see a compelling reason to block 
registration.

		- Chris

> But yeah, I'm pretty sure the intention was just that clients would 
> use
> it to communicate to each other something about the content of the
> message inside the related opaque blob that is the message, in a case
> where a user has multiple clients that all know how to decrypt the
> message, but the server doesn't.
> I have no idea where that most  idea of the server setting the flag in
> Vaibhav's most recent email came from - the whole point in the 
> original
> scenario is that the server doesn't know anything about the content of
> the email.
> Anyway, I don't think the whole way this would work has been well
> thought out yet.

I can't say I find this a particularly useful extension but I think this 
can be documented with sufficient clarity that it serves the intended 
function well enough.

