I was able to send and receive (via the hotmail extension) a set of
digitally signed messages.  (These weren't actually to hotmail.com but
rather to q.com, a service MSN provides to Qwest.)

There were no problems with messages with lines of dots.

It seems that the problem may be limited to GMail.

For reasons that I do not understand, I was not able to use the
hotmail extension to download unsigned messages.  I tried both 1.2.24
and 1.2.24b5.  In both cases, an attempt to download a single unsigned
message timed out after a very long time.  I am not especially
concerned about this, as I do not use the hotmail extension (or the
q.com address) normally.

On Jan 7, 6:42 am, Gil <[email protected]> wrote:
> I agree with Chris's point.  When I started to think about it, I
> couldn't imagine how the extension could ever download transmit mail
> in such a way to preserve the validity of a digital signature.  It
> seemed that it would be especially hard for mail that is formatted
> (e.g., sent in HTML).
>
> The reality is that, for the most part, the extension has no trouble
> preserving the validity of the signatures.  I have received many
> signed messages, and the signature coming through the extension is
> fine on all of them except those with the "lines of dots".  I have
> done diffs on "line of dots" mails received via POP and the extension,
> and the line of dots is the only difference.  And, as has been pointed
> out, GMail transmits the lines of dots correctly via its UI.
>
> Maybe GMail provides some alternative interface that the extension can
> use and that helps preserve the integrity of the message, at least in
> most cases.
>
> I tried to do a similar test with the Hotmail extension.  There, I
> wasn't able even to get the extension to download a mail with a "line
> of dots" - Thunderbird just spun.  I may have some other issues there
> - I don't use Hotmail much.
>
> On Jan 7, 12:20 am, Chris Clifton <[email protected]> wrote:
>
> > Just tried that with my own account, 7 .s sent, 7 displayed. I still
> > suspect that the problem may be due to the fact that the extension
> > "reads" the email on the website, converts it back to a POP format email
> > and finally acts as as POP server to send the message to TB. Plenty of
> > scope in that process for unintentional alteration of some trivial
> > nature, but enough to cause a digital signature to fail.
>
> > Chris Clifton wrote:
> > > What happens if you view the message on the website? If Google has
> > > already removed the period, the extension is faithfully downloading
> > > what Google displays, it can't do anything else.
>
> > > Gil wrote:
> > >> Here are some more details.
>
> > >> If I send myself a message, and the message has in it a line with just
> > >> periods (at least two), the Webmail Extension (GMail) will load the
> > >> message missing one period.
>
> > >> This happens even if there is no signature on the message.  The
> > >> signature was just the way that I detected this problem.
>
> > >> On Jan 6, 8:53 pm, Gil <[email protected]> wrote:
>
> > >>> I have diagnosed to this to where maybe it can be debugged.
>
> > >>> The email in question includes one line with the following
> > >>> text:  .......
>
> > >>> That is, my correspondent wrote a line with 7 periods in it.
>
> > >>> When I download the message using a POP server, the line comes through
> > >>> with the 7 periods, and the signature is just fine.
>
> > >>> When I download the message using the Webmail extension, the line
> > >>> comes through with only 6 periods.  The Webmail extension loses one of
> > >>> the periods somehow.
>
> > >>> Because the Webmail extension has essentially tampered with the body
> > >>> of the message (by removing a period), Thunderbird detects that fact
> > >>> (because the signature is wrong) and reports that to me.
>
> > >>> On Jan 6, 6:32 pm, Gil <[email protected]> wrote:
>
> > >>>> The sender was using Thunderbird, sending mail through their ISP's
> > >>>> SMTP server.  Hotmail was not involved.
> > >>>>       When I got home, I downloaded the message using Thunderbird and
> > >>>> GMail's POP server.  The digital signature is just fine when I
> > >>>> download it that way.
> > >>>>       Thunderbird reports the signature as invalid only if I
> > >>>> download the
> > >>>> message using the Webmail extension.  It may be that the extension is
> > >>>> modifying the message in some trivial way (e.g., deleting a trailing
> > >>>> space) that renders the signature invalid.
> > >>>>       On Jan 6, 3:00 pm, KE4AVB <[email protected]> wrote:
>
> > >>>>> Gil,
> > >>>>>         Your sender would not happen be use of the free Hotmail
> > >>>>> service would
> > >>>>> they? I have had problems sending signed and/or encrypted messages
> > >>>>> through their service. They are opening and adding Hotmail
> > >>>>> taglines to
> > >>>>> the messages sent thought their service thus invaliding the
> > >>>>> signatures
> > >>>>> and encryptions. The same problem could be happening to other service
> > >>>>> providers depending how they operate. The Hotmail problem occurs if I
> > >>>>> use the online webmail or not.
> > >>>>>         Eugene
> > >>>>>         On Jan 6, 3:45 pm, Gil <[email protected]> wrote:
>
> > >>>>>> Should the Webmail extension (with GMail - actually GAFYD) play nice
> > >>>>>> with S/MIME and digital signatures?
> > >>>>>>           I have received some signed emails using the Webmail
> > >>>>>> extension, and
> > >>>>>> Thunderbird is telling me that the signature is not valid
> > >>>>>> (message has
> > >>>>>> been modified).
> > >>>>>>           Other recipients of the same message report no problem
> > >>>>>> with the
> > >>>>>> signature - they do not use the Webmail extension but just basic
> > >>>>>> POP.
> > >>>>>>           I can't try the same, as I am behind a corporate
> > >>>>>> firewall and cannot
> > >>>>>> use POP.
> > >>>>>>           It does seems that I am able to receive some emails via
> > >>>>>> the Webmail
> > >>>>>> extension with valid signatures.  Only one sender seems to be
> > >>>>>> affected
> > >>>>>> so far.  It may be that senders using plaintext for their
> > >>>>>> messages are
> > >>>>>> not affected, but those who compose using HTML may have their
> > >>>>>> messages
> > >>>>>> corrupted (by the Webmail extension?).
> > >>>>>>           I am using:
> > >>>>>> - TB 2.0.0.23
> > >>>>>> - WebMail 1.3.5
> > >>>>>> - WebMail - GMail 0.6.5b1
>
> > --
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