Split GPG: thunderbird+enigmail stopped cache password

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cubit

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Dec 15, 2016, 4:54:04 PM12/15/16
to Qubes Users
Halo!

I have run into more problems with thunderbird+enigmail on qubes and wonder if anyone else has problems.

I have a work appvm as Debian 8 with icedove 45.5.1 and enigmail 1.8.2
I have a vault appvm with my gpg keys as Debian 8 to do split gpg.

I updated templates and dom0 today and rebooted computer.  Now when I try to look at encrypted email I am prompted to enter my gpg key password every time I look at an encrypted email.   Also if I look at an encrypted email, go to a different program and then tab back to thunderbird I am immediately asked for gpg key password for the email I was looking at.

I do notice that the password prompt window looks different from pre reboot.

Some other package info:

ii  pinentry-gtk2   0.8.3-2
ii  gnupg  1.4.18-7+deb8u3
ii  gnupg-agent   2.0.26-6+deb8u1
ii  gnupg2   2.0.26-6+deb8u1
ii  gpgv 1.4.18-7+deb8u3 
ii  libgpg-error0:amd64   1.17-3   
ii  libgpgme11:amd64  1.5.1-6 
ii  qubes-gpg-split   2.0.24-1+deb8u1   


Frustratedly
++ Cubit



cubit

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Dec 15, 2016, 4:57:34 PM12/15/16
to cubit, Qubes Users
15. Dec 2016 21:53 by cu...@tutanota.com:

I updated templates and dom0 today and rebooted computer.  Now when I try to look at encrypted email I am prompted to enter my gpg key password every time I look at an encrypted email.   Also if I look at an encrypted email, go to a different program and then tab back to thunderbird I am immediately asked for gpg key password for the email I was looking at.


Another problem I discover.  If a PGP/MIME email has an attachment. I try open it asks for password to open it.  Put correct password in and it just ask again and again and again :(



++Cubit



Marek Marczykowski-Górecki

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Dec 15, 2016, 10:37:07 PM12/15/16
to cubit, Qubes Users
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA256
The solution is easy - remove password from your keys, especially when
you're using split gpg. It is inconvenient illusion of security. If
someone gets access to your private keyring, he/she will be able to get
your password the same way. Especially when you're relying on caching it
in RAM...

The only case when password protected keys makes some sense is
protection after hardware theft, but since Qubes use full disk
encryption anyway, it doesn't add anything extra in this case.

- --
Best Regards,
Marek Marczykowski-Górecki
Invisible Things Lab
A: Because it messes up the order in which people normally read text.
Q: Why is top-posting such a bad thing?
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Version: GnuPG v2

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Andrew David Wong

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Dec 16, 2016, 12:59:09 AM12/16/16
to cubit, Qubes Users
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA512
I recommend disabling your key's passphrase (i.e., using a blank
passphrase).

See our "note on passphrases":

"You may experience trouble when attempting to use a PGP key with a
passphrase along with Split-GPG and Enigmail. If you do, you may need
to remove the passphrase from your (sub)key(s) in order to get
Split-GPG working correctly. As mentioned above, we do not believe PGP
key passphrases to be significant from a security perspective."

The reasoning can be found throughout the document (search for
"passphrase").

https://www.qubes-os.org/doc/split-gpg/

- --
Andrew David Wong (Axon)
Community Manager, Qubes OS
https://www.qubes-os.org
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cubit

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Dec 16, 2016, 6:27:47 AM12/16/16
to Andrew David Wong, Qubes Users, Marek Marczykowski-Górecki
16. Dec 2016 05:58 by a...@qubes-os.org:

I recommend disabling your key's passphrase (i.e., using a blank
passphrase).

 

This is disappointing to hear.    Removing the password sounds like a kludge than a fix to something that had been working okay.


I understand the model does not technically need a password but it is something I want (rightly or rongly) and it was working okay since R3.0 which to me indicates that it can work and just something broke.


The reasoning can be found throughout the document (search for
"passphrase").


I do and see that it is optional which should mean it works. From the page you say:


> > "Therefore, using a passphrase at all should be considered optional."


If it is not supposed to work  or is not supported it should be said  "do not use passphrase with key" instead of saying "is optional" as this lead people to understand that while not needed it works.






Andrew David Wong

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Dec 16, 2016, 7:23:00 AM12/16/16
to cubit, Qubes Users, Marek Marczykowski-Górecki
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA512

On 2016-12-16 03:27, cubit wrote:
> 16. Dec 2016 05:58 by a...@qubes-os.org:
>
>> I recommend disabling your key's passphrase (i.e., using a blank
>> passphrase).
>
>
>
> This is disappointing to hear. Removing the password sounds like
> a kludge than a fix to something that had been working okay.
>
>
>
>
>
> I understand the model does not technically need a password but it
> is something I want (rightly or rongly) and it was working okay
> since R3.0 which to me indicates that it can work and just
> something broke.
>
>
>
>
>> The reasoning can be found throughout the document (search for
>> "passphrase").
>>
>
>
>
>
> I do and see that it is optional which should mean it works. From
> the page you say:
>
>
>
>
>
>>> "Therefore,using a passphrase at all should be considered
>>> optional."
>
>
>
>
> If it is not supposed to work or is not supported it should be
> said "do not use passphrase with key" instead of saying "is
> optional" as this lead people to understand that while not needed
> it works.
>
>
>

You're taking that passage out of context. If you read it in context,
it's clear that "optional" means optional from a *security* standpoint.

You're also ignoring the part that I quoted for you previously. Here
it is again:

"You may experience trouble when attempting to use a PGP key with a
passphrase along with Split-GPG and Enigmail. If you do, you may need
to remove the passphrase from your (sub)key(s) in order to get
Split-GPG working correctly. As mentioned above, we do not believe PGP
key passphrases to be significant from a security perspective."

What this means for you:

You're experiencing trouble when attempting to use a PGP key with a
passphrase along with Split-GPG and Enigmail, so you may need to
remove the passphrase from your (sub)key(s) in order to get Split-GPG
working correctly.

- --
Andrew David Wong (Axon)
Community Manager, Qubes OS
https://www.qubes-os.org
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cubit

unread,
Dec 16, 2016, 7:42:36 AM12/16/16
to Andrew David Wong, Qubes Users, Marek Marczykowski-Górecki
16. Dec 2016 12:22 by a...@qubes-os.org:

You're also ignoring the part that I quoted for you previously. Here
it is again:

"You may experience trouble when attempting to use a PGP key with a
passphrase along with Split-GPG and Enigmail. If you do, you may need
to remove the passphrase from your (sub)key(s) in order to get
Split-GPG working correctly. As mentioned above, we do not believe PGP
key passphrases to be significant from a security perspective."

What this means for you:

You're experiencing trouble when attempting to use a PGP key with a
passphrase along with Split-GPG and Enigmail, so you may need to
remove the passphrase from your (sub)key(s) in order to get Split-GPG
working correctly.



I do not want to come across rude but that's not how I see it.   I was using passphrase fine over several releases and it just stop working for a reason I have yet to find out why.


Removing the password is not a fix it is a kludge or work around.   A fix is getting it back to its previous working state with password use intact.


If passphrase use is so seeming temperamental that you have to offer this kludge, it should be said do not use!




cubit

unread,
Dec 16, 2016, 1:23:20 PM12/16/16
to Andrew David Wong, Qubes Users, Marek Marczykowski-Górecki
16. Dec 2016 05:58 by a...@qubes-os.org:
I recommend disabling your key's passphrase (i.e., using a blank
passphrase).


Some frustrating experiments later....


+ Changing my vault VM to fedora24

   - It remembers the keys password but does not honor the timeout settings, it always reprompts at 5 minutes despite "export QUBES_GPG_AUTOACCEPT=86400" being in .bash_profile 

   - Removing the password from my subkeys and it still prompts for a password and only works with the password I removed, not blank.  interacting with gpg on command line shows that the password does not exist all signing / decryption is automatic


Any reasons for the above behavior?


+ then changing vault VM back to debian 8

  - password removed and I can now read email and attachments without being bothered when looking at each and every email.





Marek Marczykowski-Górecki

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Dec 16, 2016, 1:38:37 PM12/16/16
to cubit, Andrew David Wong, Qubes Users
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA256

On Fri, Dec 16, 2016 at 07:23:18PM +0100, cubit wrote:
> 16. Dec 2016 05:58 by a...@qubes-os.org:
>
> > I recommend disabling your key's passphrase (i.e., using a blank
> > passphrase).
> >
>
>
>
>
> Some frustrating experiments later....
>
>
>
>
> + Changing my vault VM to fedora24
>
>    - It remembers the keys password but does not honor the timeout settings, it always reprompts at 5 minutes despite "export QUBES_GPG_AUTOACCEPT=86400" being in .bash_profile 

Hmm, it works for me...

>    - Removing the password from my subkeys and it still prompts for a password and only works with the password I removed, not blank.  interacting with gpg on command line shows that the password does not exist all signing / decryption is automatic
>
> Any reasons for the above behavior?

Make sure you use gpg2, not gpg.

> + then changing vault VM back to debian 8
>
>   - password removed and I can now read email and attachments without being bothered when looking at each and every email.

- --
Best Regards,
Marek Marczykowski-Górecki
Invisible Things Lab
A: Because it messes up the order in which people normally read text.
Q: Why is top-posting such a bad thing?
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Version: GnuPG v2

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cubit

unread,
Dec 16, 2016, 1:42:29 PM12/16/16
to Marek Marczykowski-Górecki, Andrew David Wong, Qubes Users

16. Dec 2016 18:38 by marm...@invisiblethingslab.com:
+ Changing my vault VM to fedora24

   - It remembers the keys password but does not honor the timeout settings, it always reprompts at 5 minutes despite "export QUBES_GPG_AUTOACCEPT=86400" being in .bash_profile 

Hmm, it works for me...
   - Removing the password from my subkeys and it still prompts for a password and only works with the password I removed, not blank.  interacting with gpg on command line shows that the password does not exist all signing / decryption is automatic


Any reasons for the above behavior?
Make sure you use gpg2, not gpg.


Both are installed in the Fedora 24 template but if I understand correctly, the qubes gpg wrapper now defaults to gpg2.


Andrew David Wong

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Dec 17, 2016, 12:07:35 AM12/17/16
to cubit, Marek Marczykowski-Górecki, Qubes Users
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA512

Yes, but they use different keyrings, so if you update your key in one
keyring (by removing the passphrase from it), it will not necessarily
be updated in the other one.

- --
Andrew David Wong (Axon)
Community Manager, Qubes OS
https://www.qubes-os.org
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5n7xyb+qph...@guerrillamail.com

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Dec 20, 2016, 3:08:58 PM12/20/16
to qubes...@googlegroups.com
Hi,

I'm also facing the same problem. The split-gpg no longer caches the password through the set timeout on the QUBES_GPG_AUTOACCEPT variable.
I also don't want to remove the password from my private key since I used it in different devices and I don't want to use a different template as I have many things installed on my debian 8 template.
This stopped worked recently after an upgrade. Is there any way that this could be restored in the same state as it was working before?
In addition, does anyone knows how can one use the latest version of enigmail with thunderbird? The only working version of enigmail is 1.8.2 (it seems that this is a limitation from the split-gpg).


Thank you

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Jean-Philippe Ouellet

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Dec 20, 2016, 3:45:03 PM12/20/16
to 5n7xyb+qph...@guerrillamail.com, qubes...@googlegroups.com
On Tue, Dec 20, 2016 at 3:08 PM, 5n7xyb+qphld0j5ytif4l via qubes-users
<qubes...@googlegroups.com> wrote:
> I also don't want to remove the password from my private key since I used it in different devices and I don't want to use a different template as I have many things installed on my debian 8 template.

Using a separate (minimal) template may be a good idea regardless
simply to reduce the number of things which must be trusted to not be
actively malicious in order to maintain the confidentiality of your
pgp key.

I have several templates ranging from "extremely minimal" to "kitchen
sink" for exactly this reason, and would recommend the practice for
its own merit regardless of split-gpg / enigmail / whatever.

Gaea

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Dec 21, 2016, 4:21:00 AM12/21/16
to qubes...@googlegroups.com
Please what are the differences between:

Minimal:
Extremely Minimal
Full ?? VMs

Jean-Philippe Ouellet:

Jean-Philippe Ouellet

unread,
Dec 21, 2016, 1:12:15 PM12/21/16
to Gaea, qubes-users
On Wed, Dec 21, 2016 at 4:20 AM, 'Gaea' via qubes-users
<qubes...@googlegroups.com> wrote:
> Please what are the differences between:
>
> Minimal:

fedora-24-minimal + text editor, openssh, git, zsh, etc.

> Extremely Minimal

fedora-24-minimal + a text editor -- nothing else

> Full ?? VMs

All the crap. Browser, photo editor, media player, all the giant
pieces of software that pull in half the world as dependencies.


I have various others in between, such as one with only a browser (for
online banking and such).

Jean-Philippe Ouellet

unread,
Dec 21, 2016, 1:13:02 PM12/21/16
to Gaea, qubes-users
On Wed, Dec 21, 2016 at 1:11 PM, Jean-Philippe Ouellet <j...@vt.edu> wrote:
> I have various others in between, such as one with only a browser (for
> online banking and such).

I should clarify, this is a template with only a browser, and an
individual VM used for only online banking. The "and such" each have
their own respective VMs derived from the browser-only template.

5nmnvk...@guerrillamail.com

unread,
Dec 21, 2016, 2:01:57 PM12/21/16
to qubes...@googlegroups.com
Uhm I see.That's a very good idea indeed.
But anyway, reporting to my initial question, is there a way that the QUBES_GPG_AUTOACCEPT timeout could be respected without having to type the password countless times? I don't want to remove the password from my key for the reasons stated earlier.

Gaea

unread,
Dec 22, 2016, 10:52:28 PM12/22/16
to Jean-Philippe Ouellet, qubes...@googlegroups.com
Thanks Monsieur Ouellet.

I thought that there was a smaller version of Qubes that may be easier
for me. I am totally new to all this. Been with WINDOWS, but want
something more resistant to hacking & invasion of my privacy.

I managed to install Qubes 3.2. Now my google voice mail that records
MP3 like voicemail.mp3 wont play. In windows all I have to do is click
on (Play)

My laptop meets vt-d, vt-x, tpm, txt. It is UEFI, Legacy, UEFI-CSM
capable. Windows and Ubuntu which I tried both run in UEFI. But Qubes
refuses to Boot under UEFI. Tried all suggestions from forums.

I bought another hard drive to install Qubes in Legacy mode. I have to
swap Windows/Ubuntu HD & change BIOS to legacy, put in Qubes HD to fire
up QUBES. I am writing this in Qubes. Painful, but I really want to
leave WINDOWS behind. I don't see the point of running WINDOWS as a
QUBES VM.

Bye

Jean-Philippe Ouellet:

Andrew David Wong

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Dec 23, 2016, 3:38:24 AM12/23/16
to Gaea, Jean-Philippe Ouellet, qubes...@googlegroups.com
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA512

On 2016-12-22 19:51, 'Gaea' via qubes-users wrote:
> Thanks Monsieur Ouellet.
>
> I thought that there was a smaller version of Qubes that may be easier
> for me. I am totally new to all this. Been with WINDOWS, but want
> something more resistant to hacking & invasion of my privacy.
>
> I managed to install Qubes 3.2. Now my google voice mail that records
> MP3 like voicemail.mp3 wont play. In windows all I have to do is click
> on (Play)
>

It sounds like you just need a media player. I recommend VLC, which you
can download after enabling the RPMFusion repo. Instructions are here:

https://www.qubes-os.org/doc/software-update-vm/#rpmfusion-for-a-fedora-templatevm

- --
Andrew David Wong (Axon)
Community Manager, Qubes OS
https://www.qubes-os.org
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Gaea

unread,
Dec 23, 2016, 11:14:58 PM12/23/16
to Andrew David Wong, qubes...@googlegroups.com


Andrew David Wong:
> On 2016-12-22 19:51, 'Gaea' via qubes-users wrote:
>> Thanks Monsieur Ouellet.
>
>> I thought that there was a smaller version of Qubes that may be easier
>> for me. I am totally new to all this. Been with WINDOWS, but want
>> something more resistant to hacking & invasion of my privacy.
>
>> I managed to install Qubes 3.2. Now my google voice mail that records
>> MP3 like voicemail.mp3 wont play. In windows all I have to do is click
>> on (Play)
>
>
> It sounds like you just need a media player. I recommend VLC, which you
> can download after enabling the RPMFusion repo. Instructions are here:
>
> https://www.qubes-os.org/doc/software-update-vm/#rpmfusion-for-a-fedora-templatevm
>
>

Thanks Andrew.

Your suggestion works. I had actually followed web searches to RMFusion
site and other places and tried their recommendations and came up short.
And there it was in Qubes-OS docs. I am puzzeled that I did not hit it
in my searches. OR maybe I skipped Qubes-os site.

Following your pointer I was able to install VLC where others failed.
Once I had VLC installed and figured out file type associations now I
can listen to voicemail with a simple click.

Thanks

5qdxzn+46d...@guerrillamail.com

unread,
Dec 27, 2016, 11:56:42 AM12/27/16
to qubes...@googlegroups.com
So, this still doesn't work under the debian-8 template. After the update the QUBES_GPG_AUTOACCEPT stopped work and has no effect whatsoever in the cache timeout.
Therefore it would be advisable if this variable could be removed from the documentation as it does not work and could potentially lead to confusions among users.

Since I'm running out of ideas or experiments in order to have the gpg cache working again, I'll probably consider to change my template vm from debian-8 to fedora-24 (possible the minimal). Before I do that, I'd like to know from the qubes community which kind of security setup is the most advisable for the vault and icedove/thunderbird ?

Many thanks

Andrew David Wong

unread,
Dec 27, 2016, 1:15:03 PM12/27/16
to 5qdxzn+46d...@guerrillamail.com, qubes...@googlegroups.com
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA512

On 2016-12-27 08:56, 5qdxzn+46dbca9vmtsno via qubes-users wrote:
> So, this still doesn't work under the debian-8 template. After the
> update the QUBES_GPG_AUTOACCEPT stopped work and has no effect
> whatsoever in the cache timeout. Therefore it would be advisable
> if this variable could be removed from the documentation as it does
> not work and could potentially lead to confusions among users.
>

Is this with or without an empty/blank key passphrase?

> Since I'm running out of ideas or experiments in order to have the
> gpg cache working again, I'll probably consider to change my
> template vm from debian-8 to fedora-24 (possible the minimal).

Works fine for me with the default fedora-24 template.

> Before I do that, I'd like to know from the qubes community which
> kind of security setup is the most advisable for the vault and
> icedove/thunderbird ?

What exactly do you mean?

- --
Andrew David Wong (Axon)
Community Manager, Qubes OS
https://www.qubes-os.org
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5qfppt+dta...@guerrillamail.com

unread,
Dec 27, 2016, 2:34:14 PM12/27/16
to qubes...@googlegroups.com
Is this with or without an empty/blank key passphrase?

Key is protected with a passphrase


Works fine for me with the default fedora-24 template.

Between fedora-24 or fedora-24-minimal, which one is more recommended in a security perspective? What I mean is, using the standard fedora template with all apps installed on it advisable or is it preferable to use a dedicated template or a minimal bare bone template to diminish the surface attack?

Andrew David Wong

unread,
Dec 28, 2016, 2:19:43 AM12/28/16
to 5qfppt+dta...@guerrillamail.com, qubes...@googlegroups.com
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA512

On 2016-12-27 11:34, 5qfppt+dtaepv4a6ll7k via qubes-users wrote:
>> Is this with or without an empty/blank key passphrase?
>
> Key is protected with a passphrase
>

In that case, there's no need to change the documentation, since it
already works as described (i.e., without a key passphrase).

>
>> Works fine for me with the default fedora-24 template.
>
> Between fedora-24 or fedora-24-minimal, which one is more
> recommended in a security perspective? What I mean is, using the
> standard fedora template with all apps installed on it advisable or
> is it preferable to use a dedicated template or a minimal bare bone
> template to diminish the surface attack?
>

The minimal template has a smaller attack surface in general, but it
doesn't come with Split GPG pre-installed. There is probably not a
significant difference, since the Split GPG protocol tightly controls
inter-VM data transfer. There is no general recommendation here, since
the degree to which the full vs. minimal template attack surface
matters depends on your threat model. For some people, it makes more
sense to save the disk space by not having an extra minimal template
for it.

- --
Andrew David Wong (Axon)
Community Manager, Qubes OS
https://www.qubes-os.org
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5qtbx9+9hw...@guerrillamail.com

unread,
Dec 28, 2016, 9:41:43 AM12/28/16
to qubes...@googlegroups.com
In that case, there's no need to change the documentation, since it
already works as described (i.e., without a key passphrase).

Before the update was working fine with the password. Now the QUBES_GPG_AUTOACCEPT is no longer respect as one have to type in the password every single time. With all due respect, you are not trying to convert a bug into a feature and claiming that this is the expected behavior, right ?

The minimal template has a smaller attack surface in general, but it
doesn't come with Split GPG pre-installed. There is probably not a
significant difference, since the Split GPG protocol tightly controls
inter-VM data transfer. There is no general recommendation here, since
the degree to which the full vs. minimal template attack surface
matters depends on your threat model. For some people, it makes more
sense to save the disk space by not having an extra minimal template
for it.

Thank in that case I'll opt to choose the fedora 24 normal template.

Andrew David Wong

unread,
Dec 28, 2016, 1:57:33 PM12/28/16
to 5qtbx9+9hw...@guerrillamail.com, qubes...@googlegroups.com
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA512

On 2016-12-28 06:41, 5qtbx9+9hwav8wa98xp4 via qubes-users wrote:
>> In that case, there's no need to change the documentation, since
>> it already works as described (i.e., without a key passphrase).
>
> Before the update was working fine with the password. Now the
> QUBES_GPG_AUTOACCEPT is no longer respect as one have to type in
> the password every single time. With all due respect, you are not
> trying to convert a bug into a feature and claiming that this is
> the expected behavior, right ?
>

Look, we've already explained (multiple times, in this very thread)
that PGP key passphrases may have to be disabled in order to get Split
GPG to work and why this is the case. Split GPG was designed with the
expectation that there would be no passphrase on the key. If it worked
well with a passphrase before the update, that was a fortuitous
coincidence. If, after the update, it no longer works well with a
passphrase (but still works just as well without one), then this
simply doesn't qualify as a bug according to the original design.

You've identified a certain property that used to exist but that was
never intended as a feature. Now that this property has ceased to
exist, you're claiming that a feature is missing and that a bug has
been introduced. That simply doesn't follow.

I understand that you want to use a passphrase on your key despite our
arguments against it (and despite offering no counterargument), and I
respect that. It's your right to do with your keys as you please,
whatever your reasons might be. However, I'm afraid Split GPG simply
wasn't intended to accommodate you. If you'd like Split GPG to support
keys with passphrases, then you're more than welcome to submit a patch
that implements it, and we'd be grateful for your contribution!

- --
Andrew David Wong (Axon)
Community Manager, Qubes OS
https://www.qubes-os.org
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