Evolution, VPNs and Google

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Evolution, VPNs and Google

Gnome Evolution - General mailing list
Evolution 3.28.5-0ubuntu0.18.04.1
Linux Mint 19.1 Tessa
ProtonVPN and any number of others

What's the best practice for using Evolution across a VPN with GMail ?

It seems that every time I'm on a VPN either incoming, outgoing or both operations fail. Occaisionally, I'll get
a Google notice that it blocked an attempted access, but it doesn't happen consistently.

Is this one of the cases, where configure Oauth2 would be of benefit?

Mike

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Re: Evolution, VPNs and Google

Pete Biggs

>
> What's the best practice for using Evolution across a VPN with GMail
> ?
>
> It seems that every time I'm on a VPN either incoming, outgoing or
> both operations fail.

The VPN is setup at a system level - Evolution knows nothing about it.
The only issues I ever get are if I start the VPN while Evolution is
connected - presumably that's because the connections are persistent
(i.e. you don't login everytime the mail is refreshed) and the packets
get confused where they are supposed to go. I tend to get in to the
habit putting Evolution offline before starting the VPN.

>  Occaisionally, I'll get
> a Google notice that it blocked an attempted access, but it doesn't
> happen consistently.

Is it a corporate VPN or one of the internet free ones - it may be that
Google has blacklisted known sources of problems (like one of the
throw-away VPN sites).

>
> Is this one of the cases, where configure Oauth2 would be of benefit?
>
I doubt it - I'm no expert on OAuth2, but AFAIUI it's just a different
mechanism for authentication (using a token rather than a password),
other than that the connection just uses IMAP (or what Google calls
IMAP).

P.


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Re: Evolution, VPNs and Google

Patrick O'Callaghan
In reply to this post by Gnome Evolution - General mailing list
On Tue, 2019-04-16 at 18:12 -0500, Japhering via evolution-list wrote:

> Evolution  3.28.5-0ubuntu0.18.04.1
> Linux Mint 19.1 Tessa
> ProtonVPN  and any number of others
>
> What's the best practice for using Evolution across a VPN with GMail ?
>
> It seems that every time I'm on a VPN  either incoming, outgoing or
> both  operations fail.   Occaisionally,  I'll get
> a Google notice that it blocked an attempted access, but it doesn't
> happen consistently.

Can you access the Gmail account via the web interface? If so, there is
no reason for Evolution to have any problems. Evo (and Gmail) aren't
even aware they are running on a VPN and there are no configuration
options for this. If this isn't working, the problem may be with your
VPN setup. (I've used ExpressVPN without any issues.)

> Is this one of the cases, where configure Oauth2  would be of benefit?

No.

poc

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Re: Evolution, VPNs and Google

Gnome Evolution - General mailing list
It is a Gmail issue, not Evolution.  It will occur with any mail user agent software - and even with the Gmail web interface, though I don't think it blocks the latter.  Google is flagging the fact that your connection is coming from a different IP than "normal".  You can allow this access via the Gmail web i/f, but I don't know if multiple sources are stored.

This may be of interest:
https://support.google.com/mail/answer/45938?hl=en


Ed


On 4/17/19 4:13 AM, Patrick O'Callaghan wrote:
On Tue, 2019-04-16 at 18:12 -0500, Japhering via evolution-list wrote:
Evolution  3.28.5-0ubuntu0.18.04.1
Linux Mint 19.1 Tessa
ProtonVPN  and any number of others

What's the best practice for using Evolution across a VPN with GMail ?

It seems that every time I'm on a VPN  either incoming, outgoing or
both  operations fail.   Occaisionally,  I'll get
a Google notice that it blocked an attempted access, but it doesn't 
happen consistently.
Can you access the Gmail account via the web interface? If so, there is
no reason for Evolution to have any problems. Evo (and Gmail) aren't
even aware they are running on a VPN and there are no configuration
options for this. If this isn't working, the problem may be with your
VPN setup. (I've used ExpressVPN without any issues.)

Is this one of the cases, where configure Oauth2  would be of benefit?
No.

poc

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-- 
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Cinnamon 4.0.10

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Re: Evolution, VPNs and Google

Adam Tauno Williams
In reply to this post by Gnome Evolution - General mailing list
On Tue, 2019-04-16 at 18:12 -0500, Japhering via evolution-list wrote:
> Evolution 3.28.5-0ubuntu0.18.04.1
> Linux Mint 19.1 Tessa
> ProtonVPN and any number of others
> What's the best practice for using Evolution across a VPN with GMail
> ?

Unless you are activating the VPN **after** initial authentication it
shouldn't matter.  Sometimes activating a VPN changes the DNS servers,
etc... which can monkey with already active networked applications.
Otherwise it cannot make a difference.

I use Evolution to access IMAP/SMTP services over a VPN every day.

> Is this one of the cases, where configure Oauth2 would be of benefit?

Nope, not related.

--
Highland Park Neighborhood Association
Adam Tauno Williams, Board Chair
Grand Rapids, MI.
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Re: Evolution, VPNs and Google

Gnome Evolution - General mailing list
In reply to this post by Patrick O'Callaghan
Everything works without a VPN or via the web interfaces. Yet, every time I try to use Evolution across
a VPN, it typically allows receiving emails, but never, every works on sending.

And thus, I'm stumped as to why.

And yes, I start the VPN first, and then bring up Evolution after the tunnel has been established. 

Mike

On Wed, 2019-04-17 at 09:13 +0100, Patrick O'Callaghan wrote:
On Tue, 2019-04-16 at 18:12 -0500, Japhering via evolution-list wrote:
Evolution  3.28.5-0ubuntu0.18.04.1
Linux Mint 19.1 Tessa
ProtonVPN  and any number of others

What's the best practice for using Evolution across a VPN with GMail ?

It seems that every time I'm on a VPN  either incoming, outgoing or
both  operations fail.   Occaisionally,  I'll get
a Google notice that it blocked an attempted access, but it doesn't 
happen consistently.

Can you access the Gmail account via the web interface? If so, there is
no reason for Evolution to have any problems. Evo (and Gmail) aren't
even aware they are running on a VPN and there are no configuration
options for this. If this isn't working, the problem may be with your
VPN setup. (I've used ExpressVPN without any issues.)

Is this one of the cases, where configure Oauth2  would be of benefit?

No.

poc

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Re: Evolution, VPNs and Google

Gnome Evolution - General mailing list
In reply to this post by Pete Biggs
On Wed, 2019-04-17 at 09:11 +0100, Pete Biggs wrote:

What's the best practice for using Evolution across a VPN with GMail
?

It seems that every time I'm on a VPN either incoming, outgoing or
both operations fail.

The VPN is setup at a system level - Evolution knows nothing about it.
The only issues I ever get are if I start the VPN while Evolution is
connected - presumably that's because the connections are persistent
(i.e. you don't login everytime the mail is refreshed) and the packets
get confused where they are supposed to go. I tend to get in to the
habit putting Evolution offline before starting the VPN.

 Occaisionally, I'll get
a Google notice that it blocked an attempted access, but it doesn't
happen consistently.

Is it a corporate VPN or one of the internet free ones - it may be that
Google has blacklisted known sources of problems (like one of the
throw-away VPN sites).

It is ProtonVPN from the folks the provide ProtonMail. It doesn't matter, which
servers or countries.



Is this one of the cases, where configure Oauth2 would be of benefit?

I doubt it - I'm no expert on OAuth2, but AFAIUI it's just a different
mechanism for authentication (using a token rather than a password),
other than that the connection just uses IMAP (or what Google calls
IMAP).

P.


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Re: Evolution, VPNs and Google

Patrick O'Callaghan
In reply to this post by Gnome Evolution - General mailing list
On Wed, 2019-04-17 at 16:25 -0500, Japhering wrote:
> Everything works without a VPN  or via the web interfaces.  Yet,  every
> time I try to use Evolution acrossa VPN, it typically allows
> receiving  emails, but never, every works on sending.
> And thus, I'm stumped as to why.
> And yes,  I start the VPN first, and then bring up Evolution after the
> tunnel has been established.

[Please don't top-post]

How is your "Sending Email" configuration set up for the Gmail account?

poc

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Re: Evolution, VPNs and Google

Patrick O'Callaghan
In reply to this post by Gnome Evolution - General mailing list
On Wed, 2019-04-17 at 06:32 -0400, AtomicCanine via evolution-list
wrote:

> It is a Gmail issue, not Evolution.  It will occur with any mail user
> agent software - and even with the Gmail web interface, though I don't
> think it blocks the latter.  Google is flagging the fact that your
> connection is coming from a different IP than "normal".  You can allow
> this access via the Gmail web i/f, but I don't know if multiple sources
> are stored.
>
> This may be of interest:
> https://support.google.com/mail/answer/45938?hl=en
>

That page simply notes that you can check the location of recent
accesses, including those flagged as "suspicious". It says nothing
about such accesses being blocked, and if they were blocked I would
expect to be notified of the same by email, which is what Google does
for any security-related event.

I frequently used Gmail from all sorts of places, including public
spaces, friends houses, on my mobile devices, in different countries,
etc. and have never seen a blockage of this kind.

poc

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Re: Evolution, VPNs and Google

Gnome Evolution - General mailing list
In reply to this post by Pete Biggs
On Wed, 2019-04-17 at 09:11 +0100, Pete Biggs wrote:

>
> What's the best practice for using Evolution across a VPN with GMail
> ?
>
> It seems that every time I'm on a VPN either incoming, outgoing or
> both operations fail.
>
> The VPN is setup at a system level - Evolution knows nothing about
> it.
> The only issues I ever get are if I start the VPN while Evolution is
> connected - presumably that's because the connections are persistent
> (i.e. you don't login everytime the mail is refreshed) and the
> packets
> get confused where they are supposed to go. I tend to get in to the
> habit putting Evolution offline before starting the VPN.

When I'm not in my office, the boot the laptop, start the VPN and once
the VPN is setup, then and only then I start Evolution.  I've worked
this way for 30 plus years, dating back to when I was traveling the
world for big blue.

>  Occaisionally, I'll get
> a Google notice that it blocked an attempted access, but it doesn't
> happen consistently.
>
> Is it a corporate VPN or one of the internet free ones - it may be
> that
> Google has blacklisted known sources of problems (like one of the
> throw-away VPN sites).

I'm using ProtonVPN from the same folks that provide ProtonMail, a paid
version supporting many hundreds of servers.  And it doesn't matter if
I'm using a local Texas base server, a server based elsewhere in the
world or ProtonVPN's secure core servers, the behavior is the same.

The only thing that comes to mind is what type of connection is the
outbound smtp server expecting tcp or udp.  If it is udp, then that is
my problem as I typically run a tcp vpn because of some of the tools I
need only work over tcp.

Mike

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Re: Evolution, VPNs and Google

Gnome Evolution - General mailing list
In reply to this post by Patrick O'Callaghan
On Wed, 2019-04-17 at 09:13 +0100, Patrick O'Callaghan wrote:
> On Tue,
2019-04-16 at 18:12 -0500, Japhering via evolution-list
> wrote:
>
>
Evolution  3.28.5-0ubuntu0.18.04.1
> Linux Mint 19.1 Tessa
>
ProtonVPN  and any number of others
>
> What's the best practice for
using Evolution across a VPN with GMail
> ?
>
> It seems that every time
I'm on a VPN  either incoming, outgoing or
> both  operations
fail.   Occaisionally,  I'll get
> a Google notice that it blocked an
attempted access, but it doesn't
> happen consistently.
>
> Can you
access the Gmail account via the web interface? If so, there
> is
> no
reason for Evolution to have any problems. Evo (and Gmail) aren't
> even
aware they are running on a VPN and there are no configuration
> options
for this. If this isn't working, the problem may be with your
> VPN
setup. (I've used ExpressVPN without any issues.)

Evolution works flawlessly without a VPN .. and only half way when
using a VPN.

Imap
Inbound is  port 993 with TLS on a dedicated port via password
Outbound is  port 465 with TLS on a dedicated port via password

As previously stated. Receiving always works .. with or without a VPN,
while outbound only works without a VPN.

Mike
>

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Re: Evolution, VPNs and Google

Patrick O'Callaghan
In reply to this post by Patrick O'Callaghan
On Fri, 2019-04-19 at 15:23 -0500, Michael H Moran wrote:

> On Wed, 2019-04-17 at 09:13 +0100, Patrick O'Callaghan wrote:
> > On Tue, 2019-04-16 at 18:12 -0500, Japhering via evolution-list
> > wrote:
> >
> > Evolution  3.28.5-0ubuntu0.18.04.1
> > Linux Mint 19.1 Tessa
> > ProtonVPN  and any number of others
> >
> > What's the best practice for using Evolution across a VPN with GMail
> > ?
> >
> > It seems that every time I'm on a VPN  either incoming, outgoing or
> > both  operations fail.   Occaisionally,  I'll get
> > a Google notice that it blocked an attempted access, but it doesn't
> > happen consistently.
> >
> > Can you access the Gmail account via the web interface? If so, there
> > is
> > no reason for Evolution to have any problems. Evo (and Gmail) aren't
> > even aware they are running on a VPN and there are no configuration
> > options for this. If this isn't working, the problem may be with your
> > VPN setup. (I've used ExpressVPN without any issues.)
>
> Evolution works flawlessly without a VPN .. and only half way when
> using a VPN.
>
> Imap
> Inbound is  port 993 with TLS on a dedicated port via password
> Outbound is  port 465 with TLS on a dedicated port via password
>
> As previously stated. Receiving always works .. with or without a VPN,
> while outbound only works without a VPN.

I just tested it with ExpressVPN, using an Evolution session that was
already running (i.e. I turned on the VPN without restarting Evo). My
settings are the same as yours. It worked perfectly. I don't know what
to suggest other than maybe trying a different VPN to see what happens
(for example a free trial version of ExpressVPN or NordVPN).

I'm sending this reply with the VPN turned on.

poc

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Re: Evolution, VPNs and Google

Gnome Evolution - General mailing list
On Fri, 2019-04-19 at 23:01 +0100, Patrick O'Callaghan wrote:

> On Fri, 2019-04-19 at 15:23 -0500, Michael H Moran wrote:
>
> Imap
> Inbound is  port 993 with TLS on a dedicated port via password
> Outbound is  port 465 with TLS on a dedicated port via password
>
> As previously stated. Receiving always works .. with or without a
> VPN,
> while outbound only works without a VPN.
>
> I just tested it with ExpressVPN, using an Evolution session that was
> already running (i.e. I turned on the VPN without restarting Evo). My
> settings are the same as yours. It worked perfectly. I don't know
> what
> to suggest other than maybe trying a different VPN to see what
> happens
> (for example a free trial version of ExpressVPN or NordVPN).
>
So what is you base OS?  Linux? which distro base?

Mike

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Re: Evolution, VPNs and Google

Patrick O'Callaghan
On Sat, 2019-04-20 at 16:49 -0500, Japhering wrote:

> On Fri, 2019-04-19 at 23:01 +0100, Patrick O'Callaghan wrote:
> > On Fri, 2019-04-19 at 15:23 -0500, Michael H Moran wrote:
> >
> > Imap
> > Inbound is  port 993 with TLS on a dedicated port via password
> > Outbound is  port 465 with TLS on a dedicated port via password
> >
> > As previously stated. Receiving always works .. with or without a
> > VPN,
> > while outbound only works without a VPN.
> >
> > I just tested it with ExpressVPN, using an Evolution session that was
> > already running (i.e. I turned on the VPN without restarting Evo). My
> > settings are the same as yours. It worked perfectly. I don't know
> > what
> > to suggest other than maybe trying a different VPN to see what
> > happens
> > (for example a free trial version of ExpressVPN or NordVPN).
> >
> So what is you base OS?  Linux? which distro base?

Fedora 29, though I doubt that matters.

poc

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Re: Evolution, VPNs and Google

Gnome Evolution - General mailing list
On Sat, 2019-04-20 at 23:02 +0100, Patrick O'Callaghan wrote:
> On Sat, 2019-04-20 at 16:49 -0500, Japhering wrote:
>
> On Fri, 2019-04-19 at 23:01 +0100, Patrick O'Callaghan wrote:
>
> So what is you base OS?  Linux? which distro base?
>
> Fedora 29, though I doubt that matters.
>

At this point, I'm stumped.  I'm looking at the whole picture, as there
are lots of people using VPNs (ExpressVPN, NordVPN, ProtonVPN) around
the world, easy to find and converse with.  The harder part is finding
folks running Evolution on a specific VPN.

This is slowly driving me nuts.

Mike

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Re: Evolution, VPNs and Google

Pete Biggs

> At this point, I'm stumped.  I'm looking at the whole picture, as there
> are lots of people using VPNs (ExpressVPN, NordVPN, ProtonVPN) around
> the world, easy to find and converse with.  The harder part is finding
> folks running Evolution on a specific VPN.
>

When you run Evolution from the command line, do you see any errors?

How about if you run Evolution with SMTP debugging turned on?

When you have the VPN turned on can you connect to smtp.googlemail.com
from the command line using

  openssl s_client -connect smtp.googlemail.com:465

after some certificate dumps it should come up with something like

 220 smtp.googlemail.com ESMTP xxxxxxx - gsmtp

this should at least narrow down where the actual issue is.

P.


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