Re: [cryptography] Gmail and SSL

2012-12-17 Thread Uncle Zzzen
I don't understand much about CAs, but I know what paypal does: you paste
your public key (while being logged in via ssl, of course) and THEY sign it
for you.
They also show you a "key id" string (don't remember exact name) that you
should include inside the encrypted request (probably against a case where
the key gets compromised, but not the app's config). The user/password auth
pop3 has seems equivalent to that (at least to me).

PR-wise (e.g. if there's a petition), maybe it's easier to explain this to
laypeople (like me) along the lines of:
"we want google to do what paypal does, but google says:
privacy-via-bureaucracy or no privacy at all"
and only in the fine-print dive into the way CAs work.

Just a thought.


On Tue, Dec 18, 2012 at 8:18 AM, James A. Donald  wrote:

>  On 2012-12-18 1:25 AM, CodesInChaos wrote:
>
> One could require the user to specify/confirm a certificate fingerprint on
> gmail in such a case. That way you're MitM proof, even with a self signed
> certificate.
>
>
> Who is the real you?  Well, obviously the you that knows the gmail
> password.
>
> Therefore, password should no be communicated in the clear.  Gmail should
> not care whether you have a validly signed certificate, but you should care
> whether gmail has a validly signed certificate, and that it has the usual
> signature.
>
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Re: [cryptography] Gmail and SSL

2012-12-17 Thread James A. Donald

On 2012-12-18 1:25 AM, CodesInChaos wrote:
One could require the user to specify/confirm a certificate 
fingerprint on gmail in such a case. That way you're MitM proof, even 
with a self signed certificate.




Who is the real you?  Well, obviously the you that knows the gmail password.

Therefore, password should no be communicated in the clear.  Gmail 
should not care whether you have a validly signed certificate, but you 
should care whether gmail has a validly signed certificate, and that it 
has the usual signature.
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Re: [cryptography] Gmail and SSL

2012-12-17 Thread The Doctor
-BEGIN PGP SIGNED MESSAGE-
Hash: SHA1

On 12/17/2012 11:18 AM, Andy Steingruebl wrote:

> Do you have proof of that or just speculation?

CAs have been compromised.  A few: Comodo.  Diginotar.  KPN.

If a lone attcker can crack a CA and cut arbitrary certs, a
state-sponsored actor could as well.

As for buying MITM certs for DLP:

https://netsecurityit.wordpress.com/tag/data-loss-prevention/

http://www.theregister.co.uk/2012/02/09/tustwave_disavows_mitm_digital_cert/

Can a CA that's done this in the past be trusted not to do it again in
the future?  I don't think so.  If one does it, that gives the idea to
others, and they might not get caught.  There is a lot of money that
could be made selling them as well as a market for them (the same
market for DLP hardware).  See also, Jeff Walton's post earlier to
this list.

- -- 
The Doctor [412/724/301/703] [ZS|Media]
Developer, Project Byzantium: http://project-byzantium.org/

PGP: 0x807B17C1 / 7960 1CDC 85C9 0B63 8D9F  DD89 3BD8 FF2B 807B 17C1
WWW: https://drwho.virtadpt.net/

FizerPharm: Trust.  Profit.  Deniability.

-BEGIN PGP SIGNATURE-
Version: GnuPG v2.0.19 (GNU/Linux)
Comment: Using GnuPG with undefined - http://www.enigmail.net/

iEYEARECAAYFAlDPR5AACgkQO9j/K4B7F8Gr0QCgySnFFaFwKNhnC6zEdtQsAtgO
qtQAniR0Z9a/k5KJmUe0QoK3X2DUmP7I
=KJzz
-END PGP SIGNATURE-
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Re: [cryptography] Gmail and SSL

2012-12-17 Thread The Doctor
-BEGIN PGP SIGNED MESSAGE-
Hash: SHA1

On 12/15/2012 05:01 PM, James A. Donald wrote:

> Recent MITM attacks have been by entities that are likely to be
> able to coerce a CA.

Or compromise them outright.

Don't forget, there are a couple of CAs that sell signed certs for
deployment in DLP hardware, too.

- -- 
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Developer, Project Byzantium: http://project-byzantium.org/

PGP: 0x807B17C1 / 7960 1CDC 85C9 0B63 8D9F  DD89 3BD8 FF2B 807B 17C1
WWW: https://drwho.virtadpt.net/

FizerPharm: Trust.  Profit.  Deniability.

-BEGIN PGP SIGNATURE-
Version: GnuPG v2.0.19 (GNU/Linux)
Comment: Using GnuPG with undefined - http://www.enigmail.net/

iEYEARECAAYFAlDPRCwACgkQO9j/K4B7F8HMZQCcCXQo3wH9wLObfZOYG4p7u54G
lbIAnRAkWFqvt0Ecty7F6tUmz4N1qutO
=dTfC
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Re: [cryptography] Gmail and SSL

2012-12-17 Thread CodesInChaos
One could require the user to specify/confirm a certificate fingerprint on
gmail in such a case. That way you're MitM proof, even with a self signed
certificate.
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Re: [cryptography] Gmail and SSL

2012-12-16 Thread coderman
On Sat, Dec 15, 2012 at 12:23 PM, Andy Steingruebl  wrote:
> I think what you really want is the ability within Google's interface to
> specify how you'd like the certificate verified.

yes; this is what i want. for Google to arbitrarily enforce a decision
is dumb and not useful.
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Re: [cryptography] Gmail and SSL

2012-12-16 Thread Ben Laurie
On Sun, Dec 16, 2012 at 7:52 AM, ianG  wrote:
> On 16/12/12 02:41 AM, Ben Laurie wrote:
>>
>> On Sat, Dec 15, 2012 at 10:01 PM, James A. Donald 
>> wrote:
>>>
>>> On 2012-12-16 6:23 AM, Andy Steingruebl wrote:


 given some of the more recent attacks against Google (and Facebook's)
 customers they believe that active MiTM is actually a real threat, and
 would
 rather not pretend to protect you from it when they aren't, by using a
 self-signed certificate that they haven't verified in any way, even by
 you
 presenting it.
>>>
>>>
>>>
>>> Recent MITM attacks have been by entities that are likely to be able to
>>> coerce a CA.
>>
>>
>> This is why you need Certificate Transparency.
>
>
>
> Actually, we need a secure and private authentication system.  If I was
> reading that in Gmail I'd suppose that it would transparently link to here:
>
> http://www.certificate-transparency.org/
>
> ;)  As you say, that idea is a research idea.

I didn't say that (that site may say it, I don't know, I haven't been
keeping that site updated). In fact, Google is building it, right now.

>  We can only want it, we
> cannot need it.  I see several issues (4).
>
> Just looking at CAcert, by way of counter example.  CAcert does not publish
> its certificates because of privacy.  That's actually quite a strong result,
> and hard to avoid [1].

CT applies to public certificates. By definition, these are not
private. If CAcert wants to issue private certs in a CT world, then I
suspect some changes will be needed...

>  If one looks at Bitcoin or the recent many efforts
> to track all certificates, this represents a gold mine of datamining
> opportunities.  Do our customers really want their security model to become
> a public spectacle?

Public certificates are already a public spectacle. I have no idea
what Bitcoin has to do with this.

> Also (2), the notion that an auditor would be a fair arbiter of what the
> public wants is dead in the water.  It's a non-starter.

CT is not an arbiter of anything, it is an audit trail.

>  Also (3), as you
> acknowledge, getting the CAs to change anything is difficult, the OODA cycle
> is estimable at about a decade.

I think we can move faster than that. CAs have already signed up to CT.

> Which (thinking aloud) leaves cryptographic proofs that test the audit claim
> needed, without revealing the certificate body.  But that's a fairly tough
> burden.  Proving that my certificate is in the chain seems doable.  But what
> we are trying to prove is that every certificate is in the chain.  Without
> seeing every certificate.

I do not agree that that is a goal.

> Or more importantly, we want to prove that a certificate found in an MITM
> was in the chain or not.
>
> But (4) we already have that, in a non-cryptographic way.  If we find a
> certificate that is apparently signed by say VeriSign root and was found in
> an MITM, we can simply publish it with the facts.  Verisign are then
> encouraged to disclose (a) it was ours, (b) it wasn't ours, or (c)
> ummm...

The point of CT is precisely to make it possible to find MITM certs
even when you are not the victim.
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Re: [cryptography] Gmail and SSL

2012-12-15 Thread ianG

On 16/12/12 02:41 AM, Ben Laurie wrote:

On Sat, Dec 15, 2012 at 10:01 PM, James A. Donald  wrote:

On 2012-12-16 6:23 AM, Andy Steingruebl wrote:


given some of the more recent attacks against Google (and Facebook's)
customers they believe that active MiTM is actually a real threat, and would
rather not pretend to protect you from it when they aren't, by using a
self-signed certificate that they haven't verified in any way, even by you
presenting it.



Recent MITM attacks have been by entities that are likely to be able to
coerce a CA.


This is why you need Certificate Transparency.



Actually, we need a secure and private authentication system.  If I was 
reading that in Gmail I'd suppose that it would transparently link to here:


http://www.certificate-transparency.org/

;)  As you say, that idea is a research idea.  We can only want it, we 
cannot need it.  I see several issues (4).


Just looking at CAcert, by way of counter example.  CAcert does not 
publish its certificates because of privacy.  That's actually quite a 
strong result, and hard to avoid [1].  If one looks at Bitcoin or the 
recent many efforts to track all certificates, this represents a gold 
mine of datamining opportunities.  Do our customers really want their 
security model to become a public spectacle?


Also (2), the notion that an auditor would be a fair arbiter of what the 
public wants is dead in the water.  It's a non-starter.  Also (3), as 
you acknowledge, getting the CAs to change anything is difficult, the 
OODA cycle is estimable at about a decade.


Which (thinking aloud) leaves cryptographic proofs that test the audit 
claim needed, without revealing the certificate body.  But that's a 
fairly tough burden.  Proving that my certificate is in the chain seems 
doable.  But what we are trying to prove is that every certificate is in 
the chain.  Without seeing every certificate.


Or more importantly, we want to prove that a certificate found in an 
MITM was in the chain or not.


But (4) we already have that, in a non-cryptographic way.  If we find a 
certificate that is apparently signed by say VeriSign root and was found 
in an MITM, we can simply publish it with the facts.  Verisign are then 
encouraged to disclose (a) it was ours, (b) it wasn't ours, or (c) 
ummm...




iang



[1] Byzantinely again, a CA has to avoid privacy to some extent as the 
PKI architecture is a privacy disaster.

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Re: [cryptography] Gmail and SSL

2012-12-15 Thread ianG

On 16/12/12 01:01 AM, James A. Donald wrote:

On 2012-12-16 6:23 AM, Andy Steingruebl wrote:

given some of the more recent attacks against Google (and Facebook's)
customers they believe that active MiTM is actually a real threat, and
would rather not pretend to protect you from it when they aren't, by
using a self-signed certificate that they haven't verified in any way,
even by you presenting it.


Recent MITM attacks have been by entities that are likely to be able to
coerce a CA.


And, given that CA-signed client certs of a low grade are typically 
validated with an email confirmation, something that google itself 
retains core capabilities in, over & above the CAs, and indeed, the CA's 
validation will rely on google's gmail, the logic remains byzantine.


Factory-certs are generally less secure than a self-signed, 
self-presented certificate.  Indeed, musing aloud, it seems provable.


iang
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Re: [cryptography] Gmail and SSL

2012-12-15 Thread Ben Laurie
On Sat, Dec 15, 2012 at 10:01 PM, James A. Donald  wrote:
> On 2012-12-16 6:23 AM, Andy Steingruebl wrote:
>>
>> given some of the more recent attacks against Google (and Facebook's)
>> customers they believe that active MiTM is actually a real threat, and would
>> rather not pretend to protect you from it when they aren't, by using a
>> self-signed certificate that they haven't verified in any way, even by you
>> presenting it.
>
>
> Recent MITM attacks have been by entities that are likely to be able to
> coerce a CA.

This is why you need Certificate Transparency.
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Re: [cryptography] Gmail and SSL

2012-12-15 Thread James A. Donald

On 2012-12-16 6:23 AM, Andy Steingruebl wrote:
given some of the more recent attacks against Google (and Facebook's) 
customers they believe that active MiTM is actually a real threat, and 
would rather not pretend to protect you from it when they aren't, by 
using a self-signed certificate that they haven't verified in any way, 
even by you presenting it.


Recent MITM attacks have been by entities that are likely to be able to 
coerce a CA.



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Re: [cryptography] Gmail and SSL

2012-12-15 Thread Jeffrey Walton
On Sat, Dec 15, 2012 at 2:23 PM, ianG  wrote:
> ...
>
> This is a common error made by many security providers in the PKI space.
> Their security logic mistake is to assume that the self-signed signature is
> to be compared with something signed by an 'authority', rather than an
> unsigned competitor.
Right. Opportunistic encryption in email systems does not make the
system less secure when compared to plain text SMTP. When it passed
through my desk, I approved it (though something felt uncomfortable).

Jeff

> On 14/12/12 18:51 PM, Eugen Leitl wrote:
>>
>> - Forwarded message from Randy  -
>>
>> From: Randy 
>> Date: Fri, 14 Dec 2012 09:47:03 -0600
>> To: NANOG list 
>> Subject: Gmail and SSL
>> User-Agent: Mozilla/5.0 (Windows NT 6.1; WOW64;
>> rv:17.0) Gecko/17.0 Thunderbird/17.0
>>
>> I'm hoping to reach out to google's gmail engineers with this message,
>> Today I noticed that for the past 3 days, email messages from my personal
>> website's pop3 were not being received into my gmail inbox. Naturally, I
>> figured that my pop3 service was down, but after some checking, every
>> thing
>> was working OK. I then checked gmail settings, and noticed some error.
>> It explained that google is no longer accepting self signed ssl
>> certificates. It claims that this change will "offer[s] a higher level of
>> security to better protect your information".
>> I don't believe that this change offers better security. In fact it is now
>> unsecured - I am unable to use ssl with gmail, I have had to select the
>> plain-text pop3 option.
>>
>> I don't have hundreds of dollars to get my ssl certificates signed, and to
>> top it off, gmail never notified me of an error with fetching my mail. How
>> many of email accounts trying to grab mail are failing now? I bet
>> thousands, as a self signed certificate is a valid way of encrypting the
>> traffic.
>>
>> Please google, remove this requirement.
>>
>> Source:
>>
>> http://support.google.com/mail/bin/answer.py?hl=en&answer=21291&ctx=gmail#strictSSL
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Re: [cryptography] Gmail and SSL

2012-12-15 Thread Andy Steingruebl
I think what you really want is the ability within Google's interface to
specify how you'd like the certificate verified.  If the threat model they
are defending against is MiTM, then merely accepting the certificate
without prompting from you provides protection against passive
eavesdropping only, not active MiTM.  They've chosen to try and defend
against those who can tinker with packets, not just observe them.

You may disagree that this is the right threat to protect against (you
might be more worried about the NSA observing packets for example, rather
than tinkering with them) but given some of the more recent attacks against
Google (and Facebook's) customers they believe that active MiTM is actually
a real threat, and would rather not pretend to protect you from it when
they aren't, by using a self-signed certificate that they haven't verified
in any way, even by you presenting it.

The obvious solution is to either:

1. Not use TLS
2. Default to CA signed certificates
3. Support other protocols or means for you to identify what keys and/or
trust-anchors you trust.

Given that Google actually controls the client-code in this case, it might
actually a truly usable use-case for the newly minted CAA and TLSA (DANE)
specifications.  They can't be deployed most places (browsers) because of
last-mile DNS tinkering by all of the middleboxes on people's networks, but
that probably isn't the case where Google is connecting to your server,
using theirs.

Just a thought.

- Andy



On Fri, Dec 14, 2012 at 7:51 AM, Eugen Leitl  wrote:

> - Forwarded message from Randy  -
>
> From: Randy 
> Date: Fri, 14 Dec 2012 09:47:03 -0600
> To: NANOG list 
> Subject: Gmail and SSL
> User-Agent: Mozilla/5.0 (Windows NT 6.1; WOW64;
> rv:17.0) Gecko/17.0 Thunderbird/17.0
>
> I'm hoping to reach out to google's gmail engineers with this message,
> Today I noticed that for the past 3 days, email messages from my personal
> website's pop3 were not being received into my gmail inbox. Naturally, I
> figured that my pop3 service was down, but after some checking, every thing
> was working OK. I then checked gmail settings, and noticed some error.
> It explained that google is no longer accepting self signed ssl
> certificates. It claims that this change will "offer[s] a higher level of
> security to better protect your information".
> I don't believe that this change offers better security. In fact it is now
> unsecured - I am unable to use ssl with gmail, I have had to select the
> plain-text pop3 option.
>
> I don't have hundreds of dollars to get my ssl certificates signed, and to
> top it off, gmail never notified me of an error with fetching my mail. How
> many of email accounts trying to grab mail are failing now? I bet
> thousands, as a self signed certificate is a valid way of encrypting the
> traffic.
>
> Please google, remove this requirement.
>
> Source:
>
> http://support.google.com/mail/bin/answer.py?hl=en&answer=21291&ctx=gmail#strictSSL
>
> - End forwarded message -
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Re: [cryptography] Gmail and SSL

2012-12-15 Thread Jeffrey Walton
On Fri, Dec 14, 2012 at 10:51 AM, Eugen Leitl  wrote:
> - Forwarded message from Randy  -
>
> From: Randy 
> Date: Fri, 14 Dec 2012 09:47:03 -0600
> To: NANOG list 
> Subject: Gmail and SSL
> User-Agent: Mozilla/5.0 (Windows NT 6.1; WOW64;
> rv:17.0) Gecko/17.0 Thunderbird/17.0
>
> ...
>
> I don't have hundreds of dollars to get my ssl certificates signed, and to
> top it off, gmail never notified me of an error with fetching my mail. How
> many of email accounts trying to grab mail are failing now? I bet
> thousands, as a self signed certificate is a valid way of encrypting the
> traffic.
Forgot to mention I believe StartCom will give you a certificate for free.

Jeff
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Re: [cryptography] Gmail and SSL

2012-12-15 Thread ianG
The presence of a self-signed signature cannot possibly be less secure 
than the non-presence of any signature. If they are rejecting 
self-signed sigs, then they must also logically reject unsigned provision.


This is a common error made by many security providers in the PKI space. 
 Their security logic mistake is to assume that the self-signed 
signature is to be compared with something signed by an 'authority', 
rather than an unsigned competitor.


It is one of those enduring flaws that indicate that security isn't the 
objective with such systems.


iang



On 14/12/12 18:51 PM, Eugen Leitl wrote:

- Forwarded message from Randy  -

From: Randy 
Date: Fri, 14 Dec 2012 09:47:03 -0600
To: NANOG list 
Subject: Gmail and SSL
User-Agent: Mozilla/5.0 (Windows NT 6.1; WOW64;
rv:17.0) Gecko/17.0 Thunderbird/17.0

I'm hoping to reach out to google's gmail engineers with this message,
Today I noticed that for the past 3 days, email messages from my personal
website's pop3 were not being received into my gmail inbox. Naturally, I
figured that my pop3 service was down, but after some checking, every thing
was working OK. I then checked gmail settings, and noticed some error.
It explained that google is no longer accepting self signed ssl
certificates. It claims that this change will "offer[s] a higher level of
security to better protect your information".
I don't believe that this change offers better security. In fact it is now
unsecured - I am unable to use ssl with gmail, I have had to select the
plain-text pop3 option.

I don't have hundreds of dollars to get my ssl certificates signed, and to
top it off, gmail never notified me of an error with fetching my mail. How
many of email accounts trying to grab mail are failing now? I bet
thousands, as a self signed certificate is a valid way of encrypting the
traffic.

Please google, remove this requirement.

Source:
http://support.google.com/mail/bin/answer.py?hl=en&answer=21291&ctx=gmail#strictSSL

- End forwarded message -



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Re: [cryptography] Gmail and SSL

2012-12-14 Thread John Levine
>I don't have hundreds of dollars to get my ssl certificates signed, ...

I don't have a strong opinion either way about Gmail's new signing
requirement, but if the issue is money, Startcom's free certs seem to
satisfy Gmail.

Once you set up an account, it takes about five minutes to get a cert
issued.  I got one for my mail server this morning.

https://www.startssl.com/

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Re: [cryptography] Gmail and SSL

2012-12-14 Thread James A. Donald

On 2012-12-15 1:51 AM, Eugen Leitl wrote:

- Forwarded message from Randy  -

From: Randy 
Date: Fri, 14 Dec 2012 09:47:03 -0600
To: NANOG list 
Subject: Gmail and SSL
User-Agent: Mozilla/5.0 (Windows NT 6.1; WOW64;
rv:17.0) Gecko/17.0 Thunderbird/17.0

I'm hoping to reach out to google's gmail engineers with this message,
Today I noticed that for the past 3 days, email messages from my personal
website's pop3 were not being received into my gmail inbox. Naturally, I
figured that my pop3 service was down, but after some checking, every thing
was working OK. I then checked gmail settings, and noticed some error.
It explained that google is no longer accepting self signed ssl
certificates. It claims that this change will "offer[s] a higher level of
security to better protect your information".
I don't believe that this change offers better security. In fact it is now
unsecured - I am unable to use ssl with gmail, I have had to select the
plain-text pop3 option.


From the point of view of the state, the big advantage of SSL 
certificates signed by an authority, is that there are plenty of 
authorities that will sign anything the state tells them to.


If, for example, your website is e-gold.com,  this leads to problems.

Google has a propensity to favor state friendly solutions - more 
particularly, solutions friendly to the US Government, but not the 
Chinese or Russian government.



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Re: [cryptography] Gmail and SSL

2012-12-14 Thread Jeffrey Walton
On Fri, Dec 14, 2012 at 10:51 AM, Eugen Leitl  wrote:
> - Forwarded message from Randy  -
>
> From: Randy 
> Date: Fri, 14 Dec 2012 09:47:03 -0600
> To: NANOG list 
> Subject: Gmail and SSL
> User-Agent: Mozilla/5.0 (Windows NT 6.1; WOW64;
> rv:17.0) Gecko/17.0 Thunderbird/17.0
>
> I'm hoping to reach out to google's gmail engineers with this message,
> Today I noticed that for the past 3 days, email messages from my personal
> website's pop3 were not being received into my gmail inbox. Naturally, I
> figured that my pop3 service was down, but after some checking, every thing
> was working OK. I then checked gmail settings, and noticed some error.
> It explained that google is no longer accepting self signed ssl
> certificates. It claims that this change will "offer[s] a higher level of
> security to better protect your information".
> I don't believe that this change offers better security. In fact it is now
> unsecured - I am unable to use ssl with gmail, I have had to select the
> plain-text pop3 option.
>
> I don't have hundreds of dollars to get my ssl certificates signed, and to
> top it off, gmail never notified me of an error with fetching my mail. How
> many of email accounts trying to grab mail are failing now? I bet
> thousands, as a self signed certificate is a valid way of encrypting the
> traffic.
>
> Please google, remove this requirement.
>
> Source:
> http://support.google.com/mail/bin/answer.py?hl=en&answer=21291&ctx=gmail#strictSSL
Ah, interesting. I first encountered this debate in New York over
opportunistic encryption in mail servers via STARTTLS (and the
security controls surrounding it).

Jeff
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[cryptography] Gmail and SSL

2012-12-14 Thread Eugen Leitl
- Forwarded message from Randy  -

From: Randy 
Date: Fri, 14 Dec 2012 09:47:03 -0600
To: NANOG list 
Subject: Gmail and SSL
User-Agent: Mozilla/5.0 (Windows NT 6.1; WOW64;
rv:17.0) Gecko/17.0 Thunderbird/17.0

I'm hoping to reach out to google's gmail engineers with this message,
Today I noticed that for the past 3 days, email messages from my personal 
website's pop3 were not being received into my gmail inbox. Naturally, I 
figured that my pop3 service was down, but after some checking, every thing 
was working OK. I then checked gmail settings, and noticed some error.
It explained that google is no longer accepting self signed ssl  
certificates. It claims that this change will "offer[s] a higher level of 
security to better protect your information".
I don't believe that this change offers better security. In fact it is now 
unsecured - I am unable to use ssl with gmail, I have had to select the 
plain-text pop3 option.

I don't have hundreds of dollars to get my ssl certificates signed, and to 
top it off, gmail never notified me of an error with fetching my mail. How 
many of email accounts trying to grab mail are failing now? I bet 
thousands, as a self signed certificate is a valid way of encrypting the 
traffic.

Please google, remove this requirement.

Source:  
http://support.google.com/mail/bin/answer.py?hl=en&answer=21291&ctx=gmail#strictSSL

- End forwarded message -
-- 
Eugen* Leitl http://leitl.org";>leitl http://leitl.org
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