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Chris Williamson Chris Williamson
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Can't send mail via external server

I am getting e-mail errors when trying to create users in Plone 3.0.3. Also, the "Send this" document action link appears to work, but no e-mail arrives.

I'm evaluating Plone on my personal laptop. In Mail Settings, first I tried to use my Gmail account and entered the following:

SMTP Server: smtp.gmail.com
SMTP Port: 587 (the port my ISP requires me to use for other SMTP servers)
ESMTP username: chriswilliamson@gmail.com
ESMTP password: (my Gmail password)

When I try to create a user, I get the following:

Error: Failed to create your account: we were unable to send your password to your email address: (530, '5.7.0 Must issue a STARTTLS command first i15sm7857213wxd', '"Chris Williamson" <chriswilliamson@gmail.com>')

I did a little Googling and see there are some complexities (and maybe a bug) associated with Python, Zope and STARTTLS. So I try to simplify things and use my ISP's SMTP server:

SMTP Server: smtp.att.yahoo.com
SMTP Port: 465 (the port AT&T Yahoo says to use)
ESMTP Username: jchriswilliamson@sbcglobal.net
ESMTP Password: (my AT&T Yahoo password)

Now when I try to add a user I get:

Error: Failed to create your account: we were unable to send your password to your email address: Connection unexpectedly closed

Knowing that port 465 involves SSL, I try to simplify things further by using port 25, both with and without username and password. I get the same error.

I see in another post that I can work around this by turning off automatic password generation, and of course I wouldn't have this problem on a professionally hosted production site. But the 567/TLSSTART stuff makes me wonder if I need to report a bug, because I think the current Zope MailHost product is supposed to be able to do this. (There's a "Disable TLS" checkbox in the ZMI.)  And the inability to connect to the AT&T server on 465 ... it just seems I should be able to make this work.

One twist I have not mentioned: I've got Plone running on a virtual machine. All its network connections seem to be working fine. I even set up port forwarding and can connect to Plone from the host machine via localhost:8080 and via the Internet using my IP address and 8080. Maybe I need to set up some additional port forwarding, so Plone on the VM can receive data back from the external mail server? Seems unlikely though, since my normal e-mail cilent (Evolution) doesn't need me to open ports on my router to send e-mail via these servers.

Ideas? Thoughts?
Chris Williamson Chris Williamson
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Re: Can't send mail via external server

Just had an idea. I unchecked "Disable TLS" on the MailHost object in the ZMI. Now Plone can send mail via port 25.

Anyone know enough about this stuff to say if this is all the way it's supposed to work? Or do I need to let the developers know to fix something?

Thanks. :-)
Chris Williamson Chris Williamson
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Re: Can't send mail via external server

Chris Williamson wrote
Or do I need to let the developers know to fix something?
Or the documentation team know to add something?
Jere Retzer-3 Jere Retzer-3
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Re: Can't send mail via external server

In reply to this post by Chris Williamson
I'm using gmail also and have it working fine now. Under the plone setup, I'm using smtp.gmail.com, port 587, and also unchecked "disable TLS" in the ZMI

On Nov 18, 2007 2:21 PM, Chris Williamson <[hidden email]> wrote:

Just had an idea. I unchecked "Disable TLS" on the MailHost object in the
ZMI. Now Plone can send mail via port 25.

Anyone know enough about this stuff to say if this is all the way it's
supposed to work? Or do I need to let the developers know to fix something?

Thanks. :-)
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View this message in context: http://www.nabble.com/Can%27t-send-mail-via-external-server-tf4832075s15482.html#a13824621
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Chris Williamson Chris Williamson
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Re: Can't send mail via external server

jere.r wrote
I'm using gmail also and have it working fine now. Under the plone setup,
I'm using smtp.gmail.com, port 587, and also unchecked "disable TLS" in the
ZMI
Thanks for confirming this is doable.

Once again reviewing the unified installer's README, I see I needed to install libssl-dev (which I did not do) as well as libssl (which I did) before running the Plone installer. So installed libssl-dev, restarted Plone, unchecked "Disable TLS" and tried the Gmail server again, and I got something a little different:

Error: Failed to create your account: we were unable to send your password to your email address: SMTP AUTH extension not supported by server.
binet1 binet1
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Re: Can't send mail via external server

This post has NOT been accepted by the mailing list yet.

Chris Williamson wrote
jere.r wrote
I'm using gmail also and have it working fine now. Under the plone setup,
I'm using smtp.gmail.com, port 587, and also unchecked "disable TLS" in the
ZMI
Thanks for confirming this is doable.

Once again reviewing the unified installer's README, I see I needed to install libssl-dev (which I did not do) as well as libssl (which I did) before running the Plone installer. So installed libssl-dev, restarted Plone, unchecked "Disable TLS" and tried the Gmail server again, and I got something a little different:

Error: Failed to create your account: we were unable to send your password to your email address: SMTP AUTH extension not supported by server.
i use thunderbird i trying port forwarding for port 25 but don't word
after i have in my smtp setting account unchecked teh cas "use name and password" and this work fine. I can send mail now
srikky srikky
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Re: Can't send mail via external server

This post has NOT been accepted by the mailing list yet.
In reply to this post by Chris Williamson

Chris Williamson wrote
I am getting e-mail errors when trying to create users in Plone 3.0.3. Also, the "Send this" document action link appears to work, but no e-mail arrives.

I'm evaluating Plone on my personal laptop. In Mail Settings, first I tried to use my Gmail account and entered the following:

SMTP Server: smtp.gmail.com
SMTP Port: 587 (the port my ISP requires me to use for other SMTP servers)
ESMTP username: chriswilliamson@gmail.com
ESMTP password: (my Gmail password)

When I try to create a user, I get the following:

Error: Failed to create your account: we were unable to send your password to your email address: (530, '5.7.0 Must issue a STARTTLS command first i15sm7857213wxd', '"Chris Williamson" <chriswilliamson@gmail.com>')

I did a little Googling and see there are some complexities (and maybe a bug) associated with Python, Zope and STARTTLS. So I try to simplify things and use my ISP's SMTP server:

SMTP Server: smtp.att.yahoo.com
SMTP Port: 465 (the port AT&T Yahoo says to use)
ESMTP Username: jchriswilliamson@sbcglobal.net
ESMTP Password: (my AT&T Yahoo password)

Now when I try to add a user I get:

Error: Failed to create your account: we were unable to send your password to your email address: Connection unexpectedly closed

Knowing that port 465 involves SSL, I try to simplify things further by using port 25, both with and without username and password. I get the same error.

I see in another post that I can work around this by turning off automatic password generation, and of course I wouldn't have this problem on a professionally hosted production site. But the 567/TLSSTART stuff makes me wonder if I need to report a bug, because I think the current Zope MailHost product is supposed to be able to do this. (There's a "Disable TLS" checkbox in the ZMI.)  And the inability to connect to the AT&T server on 465 ... it just seems I should be able to make this work.

One twist I have not mentioned: I've got Plone running on a virtual machine. All its network connections seem to be working fine. I even set up port forwarding and can connect to Plone from the host machine via localhost:8080 and via the Internet using my IP address and 8080. Maybe I need to set up some additional port forwarding, so Plone on the VM can receive data back from the external mail server? Seems unlikely though, since my normal e-mail cilent (Evolution) doesn't need me to open ports on my router to send e-mail via these servers.

Ideas? Thoughts?
I have had some problems configuring the mail host. I messed with one of the instances of the plone on which the mail host was working perfect. i created a new instance of standalone plone and tried to configure the mail host. However, the following error pops up when i try to add new users:
"Failed to create your account: we were unable to send your password to your email address: len() of unsized object"
This error was something different from other listed here. Did anyone have the same problem? Is there a fix?
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