Re: [gentoo-user] encrypting emails on more than one email account with same keys

2019-05-24 Thread Mick
On Friday, 24 May 2019 04:58:02 BST Grant Taylor wrote:
> On 5/23/19 9:49 PM, mad.scientist.at.la...@tutanota.com wrote:
> > I suspect most lawyers would agree that email is just a bad idea
> > if confidentiality matters, or the web in general frankly and it's
> > getting worse fast.

Yes, face to face seems to work best, but it is not always convenient/
possible.


> I find that S/MIME works quite well for me.  It's also largely
> transparent once it's configured.

... And with 'eFail' the same could end up happening with the previously 
encrypted text!

https://www.paubox.com/blog/pgp-smime-efail-flaw
https://www.kb.cert.org/vuls/id/122919/
https://bugs.gentoo.org/683034

-- 
Regards,
Mick

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Re: [gentoo-user] encrypting emails on more than one email account with same keys

2019-05-23 Thread Grant Taylor

On 5/23/19 9:49 PM, mad.scientist.at.la...@tutanota.com wrote:
I suspect most lawyers would agree that email is just a bad idea 
if confidentiality matters, or the web in general frankly and it's 
getting worse fast.


I find that S/MIME works quite well for me.  It's also largely 
transparent once it's configured.


I also find that in general email's (and Usenet's) store-and-forward 
networking work quite well, even without being able to establish 
end-to-end connections.




Re: [gentoo-user] encrypting emails on more than one email account with same keys

2019-05-23 Thread mad.scientist.at.large
sorry, obviously i mis-sent that.

"We the People Dare to Create a More Perfect Union" 



May 23, 2019, 9:49 PM by mad.scientist.at.la...@tutanota.com:

> I use Tutanota.com, they allow multiple open sessions, many people can look 
> at/use the same email address if they all have the email addr. and password.  
> I suspect other encrypted mail providers do the same.  However, if it's 
> actually of value i'd use something more secure.  You can always encrypt 
> documents and send them out over any old email, likely far more securely than 
> plaintext sent encrypted via mail server.  They did have a security flaw in 
> the tutanota software months ago and people got into mail boxes, I've since 
> seen a small amount of spam (I usually get none, aggressive pursuit works!) 
> demonstrating again that humans are usually the weakest part of any security 
> system.  So, how much do you trust people you haven't met?   I suspect most 
> lawyers would agree that email is just a bad idea if confidentiality matters, 
> or the web in general frankly and it's getting worse fast.
>
> "We the People Dare to Create a More Perfect Union" 
>
>
>
> May 23, 2019, 9:39 PM by gtay...@gentoo.tnetconsulting.net:
>
>> On 5/23/19 1:11 PM, Dale wrote:
>>
>>> I have to deal with a State entity for some communications and they do that 
>>> send a link thing to go to a Cisco site to get/send emails. I guess it is 
>>> somewhat better than just plain open email but as you point out, if they 
>>> have the email with the link, they do the same as the intended recipient 
>>> and get the encrypted email too.
>>>
>>
>> Some of these types of sites, most that I've used, configure something out 
>> of band, usually a password, such that you have to have that to get logged 
>> in to see the message(s) in the future.
>>
>> I know that my insurance, my bank, and my CC company do this.  Just having 
>> the link is not sufficient to be able to read the ""secure message.
>>




Re: [gentoo-user] encrypting emails on more than one email account with same keys

2019-05-23 Thread mad.scientist.at.large
I use Tutanota.com, they allow multiple open sessions, many people can look 
at/use the same email address if they all have the email addr. and password.  I 
suspect other encrypted mail providers do the same.  However, if it's actually 
of value i'd use something more secure.  You can always encrypt documents and 
send them out over any old email, likely far more securely than plaintext sent 
encrypted via mail server.  They did have a security flaw in the tutanota 
software months ago and people got into mail boxes, I've since seen a small 
amount of spam (I usually get none, aggressive pursuit works!) demonstrating 
again that humans are usually the weakest part of any security system.  So, how 
much do you trust people you haven't met?   I suspect most lawyers would agree 
that email is just a bad idea if confidentiality matters, or the web in general 
frankly and it's getting worse fast.

"We the People Dare to Create a More Perfect Union" 



May 23, 2019, 9:39 PM by gtay...@gentoo.tnetconsulting.net:

> On 5/23/19 1:11 PM, Dale wrote:
>
>> I have to deal with a State entity for some communications and they do that 
>> send a link thing to go to a Cisco site to get/send emails. I guess it is 
>> somewhat better than just plain open email but as you point out, if they 
>> have the email with the link, they do the same as the intended recipient and 
>> get the encrypted email too.
>>
>
> Some of these types of sites, most that I've used, configure something out of 
> band, usually a password, such that you have to have that to get logged in to 
> see the message(s) in the future.
>
> I know that my insurance, my bank, and my CC company do this.  Just having 
> the link is not sufficient to be able to read the ""secure message.
>




Re: [gentoo-user] encrypting emails on more than one email account with same keys

2019-05-23 Thread Grant Taylor

On 5/23/19 1:11 PM, Dale wrote:
I have to deal with a State entity for some communications and they 
do that send a link thing to go to a Cisco site to get/send emails. 
I guess it is somewhat better than just plain open email but as you 
point out, if they have the email with the link, they do the same as 
the intended recipient and get the encrypted email too.


Some of these types of sites, most that I've used, configure something 
out of band, usually a password, such that you have to have that to get 
logged in to see the message(s) in the future.


I know that my insurance, my bank, and my CC company do this.  Just 
having the link is not sufficient to be able to read the ""secure message.




Re: [gentoo-user] encrypting emails on more than one email account with same keys

2019-05-23 Thread Grant Taylor

Re-sending because this didn't show up in the mailing list.

On 5/23/19 9:40 AM, Dale wrote:

Howdy,


Hi,

I'm trying to get some legal work done.  I'm trying to do this over email 
with a lawyer.  For obvious reasons, I want to do this encrypted but 
suspect they are not set up for this.  They have two email accounts that I 
know of.  Is it possible to have one set of keys and one password to work 
on two different email accounts with two different addresses?  Example, 
one account is g...@hisisp.com and his paralegal helper is a...@hisisp.com. 
They are both on the same server and it is a private server, not yahoo, 
gmail or something.


I don't know of any email based encryption techniques that support this. 
   S/MIME can encrypt messages to both recipients if you have 
certificates for them.  I think PGP can do the same.  But both 
techniques use discreet certificates / key pairs per party.


If you trust their server, and your server, you might be able to get by 
without dealing with encryption in the email and instead relying on 
encryption between the servers.  -  There are some more nuances to this, 
but it can be made to work.




--
Grant. . . .
unix || die





Re: [gentoo-user] encrypting emails on more than one email account with same keys

2019-05-23 Thread Dale
Rich Freeman wrote:
> On Thu, May 23, 2019 at 12:49 PM Mick  wrote:
>> On Thursday, 23 May 2019 16:40:23 BST Dale wrote:
>>> Howdy,
>>>
>>> I'm trying to get some legal work done.  I'm trying to do this over
>>> email with a lawyer.  For obvious reasons, I want to do this encrypted
>>> but suspect they are not set up for this.
>> Have you asked them?  If they have some setup they use to ensure client
>> confidentiality and data privacy, you'd be much better off to jump onto their
>> system, rather than trying to negotiate the configuration of PGP and S/MIME
>> with legal staff who may have zero technical capability and 
>> poor/uncooperative
>> IT support.
> ++
>
> >From what I've seen these sorts of systems are usually just security
> theater, such as emailing you a link to go to an SSL website to view
> the "secure" message, never mind that somebody else could do the same
> thing if they intercepted your email.  But, it probably satisfies some
> box-checker because the actual message is transmitted over SSL.
>
> I think this is probably the best you're going to do if you're not
> communicating with people who get crypto, which is just about
> everybody.
>
> Otherwise the rest of the email already covered some of the details.
> You can just add multiple identities to a single GPG key or x509
> certificate, but if they aren't already using PKI/etc that seems like
> a huge uphill battle.
>
> I think a corporate environment is much more likely to be using
> S/MIME/etc than GPG.  When I've seen these there is usually a central
> CA that has some way to systematically assign certificates to
> employees.  Often this is only done on request.
>
> Law firms are also notoriously bad at IT from what I've seen.  I know
> a lawyer or two and many of these firms just let every partner do
> things their own way, and their individual staff follow the partner's
> lead.  They're as bad as doctors, especially since the whole EMR thing
> hasn't hit lawyers in the same way.
>


Well, I got a reply.  They are not set up for encryption and don't seem
to be interested in it either. There is only two of them, that I know
of.  It's a small town lawyer but I like the guy.  Rare for me to like a
lawyer.  lol  What I was hoping is to have two email address, one for
each, but a single password.  I couldn't find anything that showed that
as doable so I thought I'd ask, out of curiosity if nothing else. 

I have to deal with a State entity for some communications and they do
that send a link thing to go to a Cisco site to get/send emails.  I
guess it is somewhat better than just plain open email but as you point
out, if they have the email with the link, they do the same as the
intended recipient and get the encrypted email too.

They are building a new cell phone tower but have not turned it on yet. 
They working on it tho.  I'm hoping I'm not so close that I can't get a
signal from it, umbrella effect I think it is called.  Anyway, the best
way to get me is email.  Most of the time my cell has no signal.  For
that reason, I wish Lawyers, Doctors and some others would use some sort
of secure messaging system so that I can do things without being snooped
on.  Sadly, other than the State entity mentioned above, no one else
does this.  To be honest, the only reason I set up encryption is that I
have one friend who wants to do it that way and won't send emails unless
they are.  It doesn't matter what is in it either.  Since I have it tho,
I wish more would use it.  There are times when I need to do things or
even send attachments that I wouldn't want everyone seeing.  I'm not
sure why people who deal with sensitive info won't get some secure way
of emailing.  It's weird to me. 

At least I have my answer and learned a few other things as well. 

Thanks to all. 

Dale

:-)  :-) 



Re: [gentoo-user] encrypting emails on more than one email account with same keys

2019-05-23 Thread Rich Freeman
On Thu, May 23, 2019 at 12:49 PM Mick  wrote:
>
> On Thursday, 23 May 2019 16:40:23 BST Dale wrote:
> > Howdy,
> >
> > I'm trying to get some legal work done.  I'm trying to do this over
> > email with a lawyer.  For obvious reasons, I want to do this encrypted
> > but suspect they are not set up for this.
>
> Have you asked them?  If they have some setup they use to ensure client
> confidentiality and data privacy, you'd be much better off to jump onto their
> system, rather than trying to negotiate the configuration of PGP and S/MIME
> with legal staff who may have zero technical capability and poor/uncooperative
> IT support.

++

>From what I've seen these sorts of systems are usually just security
theater, such as emailing you a link to go to an SSL website to view
the "secure" message, never mind that somebody else could do the same
thing if they intercepted your email.  But, it probably satisfies some
box-checker because the actual message is transmitted over SSL.

I think this is probably the best you're going to do if you're not
communicating with people who get crypto, which is just about
everybody.

Otherwise the rest of the email already covered some of the details.
You can just add multiple identities to a single GPG key or x509
certificate, but if they aren't already using PKI/etc that seems like
a huge uphill battle.

I think a corporate environment is much more likely to be using
S/MIME/etc than GPG.  When I've seen these there is usually a central
CA that has some way to systematically assign certificates to
employees.  Often this is only done on request.

Law firms are also notoriously bad at IT from what I've seen.  I know
a lawyer or two and many of these firms just let every partner do
things their own way, and their individual staff follow the partner's
lead.  They're as bad as doctors, especially since the whole EMR thing
hasn't hit lawyers in the same way.

-- 
Rich



Re: [gentoo-user] encrypting emails on more than one email account with same keys

2019-05-23 Thread Mick
On Thursday, 23 May 2019 16:40:23 BST Dale wrote:
> Howdy,
> 
> I'm trying to get some legal work done.  I'm trying to do this over
> email with a lawyer.  For obvious reasons, I want to do this encrypted
> but suspect they are not set up for this.  

Have you asked them?  If they have some setup they use to ensure client 
confidentiality and data privacy, you'd be much better off to jump onto their 
system, rather than trying to negotiate the configuration of PGP and S/MIME 
with legal staff who may have zero technical capability and poor/uncooperative 
IT support.


> They have two email accounts
> that I know of.  Is it possible to have one set of keys and one password
> to work on two different email accounts with two different addresses? 
> Example, one account is g...@hisisp.com and his paralegal helper is
> a...@hisisp.com.  They are both on the same server and it is a private
> server, not yahoo, gmail or something. 
> 
> I tried to google this but didn't see anything that answers this, which
> makes me think this can't be done or isn't a good thing to do.
> 
> Thanks much. 
> 
> Dale
> 
> :-)  :-) 


GnuPG can be configured with various subkeys.  So, one gpg master key can have 
multiple subkeys, each with different email addresses and different or the 
same passwords.  However, why would you need the same key for two different 
email recipients?

You may want to clarify what it is you intend to encrypt?  Email content?  
Documents?  Both?

You could encrypt email messages with gpg or S/MIME which uses TLS 
certificates - neither are easy unless the recipients are technically clued 
up.

You could encrypt word documents with TLS certificates - MSWord and 
LibreOffice can work with those, but the certificate will need to be imported 
and accepted as 'trusted' in the OS certificate manager, unless it has been 
issued by one of the expensive CAs which are included in the MSWindows OS (I 
am assuming they are using MSWindows).  Adobe reader is more difficult with 
TLS certificates.  From what I recall it wants one of its own associated (and 
expensive) CAs to be used, or it will refuse to work.  There are other PDF 
readers, but I don't know how receptive they are to free or self-signed TLS 
certificates.

You could also use a zip application with a pre-shared password - 7zip is 
free, easy to use and will work with strong encryption, assuming the lawyers 
can install it on their systems. 

Rather than trying to navigate the complexity of setting up gpg or S/MIME 
certificates, configuring email clients, individual OS' certificate managers, 
training lawyers to use them and hoping they will not at some point click the 
send button while forgetting to encrypt the message, it may be much simpler to 
use 7zip for documents sent in unencrypted email.

Alternatively, if you/they have access to a file server you could set up a 
secure area for uploading/downloading documents to/from, rather than pinging 
messages over various email servers.  A server at your home address would be 
best, as you could lock it down to only accept connections from specific IP 
addresses and user accounts, which you will set up and control yourself.

-- 
Regards,
Mick

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