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Sending newsletters from a Mac

[joshi, sunil]sunil joshi - 01:56pm Jul 18, 2006 PST

Hi, I am trying to use my iBook to send out newsletters to my family and friends, and after a long search I have found phpList might be the right solution. I was able to configure phplist on my isp host, but their email use policies have made it difficult for me to use it on the hosted web account. Hence the decision to set up a smtp server on my laptop and use phplist on it to send out newsletters. But in trying to set it up, I have been stumped! phpList seems to be working fine (I say this because I am able to send the emails to the process que and the process que runs fine), but no newsletters get sent out.

I used "postfix enabler" to enable postfix and we know that the laptop smtp server is working because when I try to send out emails from mail.app using localhost as the smtp server, it seems to be working fine.

So the question is, why do none of my emails go out through phpList. Does any one have any experience setting up phpList? It seems like a great software for sending out emails to a list, but I have been stumped in trying to set it up on my iBook.

Oh, one final thing, I am behind the AirPort so the laptop is not directly linked to the web. Does it make any difference?



[I can't answer the question, but I'd wonder why you decided that simply BCCing all the recipients wouldn't work? -Adam]


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sunil joshi - Jul 19, 2006 2:54 pm (#1 Total: 18)  

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Re: Sending newsletters from a Mac

bcc is indeed one possibility. But now that I have started down this road, it is bothersome that I cannot figure it out!

If nothing else works, I guess that would be the last resort.

Bill Poupore (apparently) - Jul 19, 2006 2:54 pm (#2 Total: 18)  

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Re: Sending newsletters from a Mac

>[I can't answer the question, but I'd wonder why you decided that simply BCCing all the recipients wouldn't work? -Adam]

Rather than BCCing, which can seem inpersonal, there are other programs available that will do what you'e trying to do with phpList without a hassle. I use Email Merge from Sig Software, but I recall seeing other similiar programs in the past.
Email Merge will use a list of email addresses from the clipboard, a text file, or a Filemaker database, and allows each message to be personalized. It sends the customized messages to your email program, via Applescript I believe, to do the actual sending.

<http://www.sigsoftware.com/emailmerge/>

I think it will do exactly what you need, and is very simple to use. There is a 28 evaluation period so you can give it a good try before commiting to buy it. During the evaluation period you're limited to 20 messages at a time.

I don't have any connection to Sig Software except as a very satisfied long time user of Email Merge.

Bill

Chris Pepper (apparently) - Jul 19, 2006 2:54 pm (#3 Total: 18)  

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Re: Sending newsletters from a Mac

At 1:56 PM -0700 2006/07/18, sunil joshi wrote:
>Hi, I am trying to use my iBook to send out newsletters to my family
>and friends, and after a long search I have found phpList might be
>the right solution. I was able to configure phplist on my isp host,
>but their email use policies have made it difficult for me to use it
>on the hosted web account. Hence the decision to set up a smtp
>server on my laptop and use phplist on it to send out newsletters.
>But in trying to set it up, I have been stumped! phpList seems to be
>working fine (I say this because I am able to send the emails to the
>process que and the process que runs fine), but no newsletters get
>sent out.
>
>I used "postfix enabler" to enable postfix and we know that the
>laptop smtp server is working because when I try to send out emails
>from mail.app using localhost as the smtp server, it seems to be
>working fine.
>
>So the question is, why do none of my emails go out through phpList.
>Does any one have any experience setting up phpList? It seems like a
>great software for sending out emails to a list, but I have been
>stumped in trying to set it up on my iBook.

        Spam filters? Most spam these days comes from (through) SMTP
servers installed by viruses/trojans on broadband-connected home
computers. As a result, many mail servers simply drop anything coming
from a home (dynamic) IP. Running Postfix from a normal home or
travel IP is going to be quite problematic.


                                                Chris
--
Chris Pepper: <http://www.reppep.com/~pepper/>
Rockefeller University: <http://www.rockefeller.edu/>

Geoff.Odhner (apparently) - Jul 20, 2006 3:02 pm (#4 Total: 18)  

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Re: Sending newsletters from a Mac

On Jul 19, 2006, at 5:54 PM, Bill Poupore wrote:
>> [I can't answer the question, but I'd wonder why you decided that
>> simply BCCing all the recipients wouldn't work? -Adam]
>
> Rather than BCCing, which can seem inpersonal, there are other
> programs available that will do what you'e trying to do with
> phpList without a hassle. I use Email Merge from Sig Software,
> but I recall seeing other similiar programs in the past.
> Email Merge will use a list of email addresses from the clipboard,
> a text file, or a Filemaker database, and allows each message to be
> personalized. It sends the customized messages to your email
> program, via Applescript I believe, to do the actual sending.
>
> <http://www.sigsoftware.com/emailmerge/>

Another such program is Direct Mail, which I've used and which works
well.

<http://ethreesoftware.com/directmail/index.php>

>
> I think it will do exactly what you need, and is very simple to
> use. There is a 28 evaluation period so you can give it a good try
> before commiting to buy it. During the evaluation period you're
> limited to 20 messages at a time.
>
> I don't have any connection to Sig Software except as a very
> satisfied long time user of Email Merge.

Likewise with respect to my relationship to e3 Software.

Geoff
.

sunil joshi - Jul 20, 2006 3:02 pm (#5 Total: 18)  

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Re: Sending newsletters from a Mac

Chris, thats interesting. But I don't belive spam filters is the problem, because when I send an email using mail.app and using localhost as the smtp server, it reaches my other accounts. - thanks.

sunil joshi - Jul 20, 2006 3:02 pm (#6 Total: 18)  

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Re: Sending newsletters from a Mac

Chris, thanks for the advice. I will look into emailmerge which sounds like a useful program to customize emails. One reason to look into phplist was that it allows complex formatting using template system and css. Also it has a opensource (mysql) backend database, and I am a big fan of opensource - eventhough can be clunkier than the great programs available for mac.

michael (apparently) - Jul 20, 2006 3:04 pm (#7 Total: 18)  

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Re: Sending newsletters from a Mac

Hello

I use emerge:

http://www.galleon.com/emerge/index.html

I send out 6,000 newsletters a month with it. There is a free demo.

Regards
Michael

E-mail: michaelmayo-ireland.ie

barry.wainwright (apparently) - Jul 22, 2006 12:36 pm (#8 Total: 18)  

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Re: Sending newsletters from a Mac

On 18/7/06 21:56, "sunil joshi" <pavansutcomcast.net> wrote:

Hi, I am trying to use my iBook to send out newsletters to my family and friends, and after a long search I have found phpList might be the right solution.  I was able to configure phplist on my isp host, but their email use policies have made it difficult for me to use it on the hosted web account.  Hence the decision to set up a smtp server on my laptop and use phplist on it to send out newsletters.  But in trying to set it up, I have been stumped!  phpList seems to be working fine (I say this because I am able to send the emails to the process que and the process que runs fine), but no newsletters get sent out.   

Amongst all the other solutions suggested, I wonder why you don’t use a ‘one stop shop’ as your solution.

If you have Microsoft Office installed, you can create your newsletter in Word, and use the ‘mail merge to email’ function to send out a personalised copy of it to each recipient in the Office/Entourage address book (or any sub-set of recipients you choose to define)

--
Barry

John_Wolff - Jul 24, 2006 2:25 am (#9 Total: 18)  

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Re: Sending newsletters from a Mac

Hi All,

Many thanks to Geoffrey Odhner for his suggestion of Direct Mail. This is a beautifully crafted piece of software. I think it has (and I sincerely hope so!) solved a problem for our weekly e-letter which has, of late, been munched due to our ISP's smtp server being blacklisted and limiting our use of the BCC field for hundreds of addresses.

What Direct Mail seems to have is its own built in mail server but I presume it is invoking the normally dormant Sendmail code within OS X. Is this correct?

What is not clear though, is whether that code, once activated, is creating a security hole that spammers can exploit. That would be like jumping from a hot frying pan right into the fire!

Cheers,

John Wolff Grandmother's Garden Patchwork & Quilting Hamilton, New Zealand.

Geoff.Odhner (apparently) - Jul 25, 2006 10:34 am (#10 Total: 18)  

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On Jul 24, 2006, at 5:25 AM, John_Wolff wrote:
> Hi All,
>
> Many thanks to Geoffrey Odhner for his suggestion of Direct Mail.
> This is a beautifully crafted piece of software. I think it has
> (and I sincerely hope so!) solved a problem for our weekly e-letter
> which has, of late, been munched due to our ISP's smtp server being
> blacklisted and limiting our use of the BCC field for hundreds of
> addresses.
>
> What Direct Mail seems to have is its own built in mail server but
> I presume it is invoking the normally dormant Sendmail code within
> OS X. Is this correct?

I believe that is what it is doing. It has a mode which it calls
"direct delivery support", which it says will "bypass your ISP's SMTP
server". It says further "Direct Mail gives you the option of
sending the messages directly to the recipient's mail server, or
routing them through your ISP's SMTP server." Here's the header from
a test email which I sent to myself just a few minutes ago to find out:

From: Geoff_OdhnerFranklin.com
Subject: test mail
Date: July 24, 2006 9:47:00 PM EDT
To: odhnerpobox.com
Return-Path: <SRS0=cjSb=BK=Franklin.com=Geoff_Odhner@bounce2.pobox.com>
Received: from kelvin.pobox.com (kelvin.pobox.com [207.8.226.2]) by
pro60.cedant.com (8.13.6/8.13.6) with ESMTP id k6P1mSK3045863 for
<ggoodhner.net>; Mon, 24 Jul 2006 18:48:31 -0700 (PDT) (envelope-
from SRS0=cjSb=BK=Franklin.com=Geoff_Odhner@bounce2.pobox.com)
Received: from anemone.local
(pool-70-104-90-61.pskn.east.verizon.net [70.104.90.61]) by
kelvin.pobox.com (Postfix) with SMTP id 224711408BB for
<odhnerpobox.com>; Mon, 24 Jul 2006 21:47:29 -0400 (EDT)
X-Mailer: Direct Mail for Mac OS X
Mime-Version: 1.0
Content-Type: multipart/alternative; boundary=Direct-Mail-MIME-
Boundary-1
Message-Id: <20060725014729.224711408BBkelvin.pobox.com>
X-Spam-Score: 1.865
(FORGED_RCVD_HELO,HTML_MESSAGE,HTML_SHORT_LENGTH,MPART_ALT_DIFF,SPF_HELO
_PASS,SPF_PASS)

 From this header you can see that DirectMail initiated the mailing
on my local machine, anemone, and sent it directly to
kelvin.pobox.com, the initial destination, which is a forwarder,
which forwarded it to my primary account on odhner.net, which is a
domain hosted on the domain pro60.cedant.com.


> What is not clear though, is whether that code, once activated, is
> creating a security hole that spammers can exploit. That would be
> like jumping from a hot frying pan right into the fire!

Yes, this approach could facilitate spamming, I'm afraid. It's
certainly not why I got this software, and I did think twice before
buying it, because I don't like to support a software vendor who's
intentions are to support spammers, but since I don't really know his
intentions, I bought the software I need. On the other hand, if
you're asking whether this creates a hole in *your* system that
spammers can exploit, then I really don't think so. It's just like
any other program you run that initiates a connection to the outside
world. Unless you have an existing hole already, this should make no
difference to your security.

Best regards,

Geoff Odhner
.

dwurster - Jul 25, 2006 10:34 am (#11 Total: 18)  

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Re: Sending newsletters from a Mac

Have you considered MaxBulkMailer?

http://www.nicholaspyers.com/articles/20020420-maxbulkmailer/index.html

It has lots of options about how it connects to your mail server. Perhaps you can creatively find some settings that will 'play nice' with your ISP.

Geoff.Odhner (apparently) - Jul 25, 2006 10:34 am (#12 Total: 18)  

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On Jul 24, 2006, at 5:25 AM, John_Wolff wrote:
> Hi All,
>
> Many thanks to Geoffrey Odhner for his suggestion of Direct Mail.
> This is a beautifully crafted piece of software. I think it has
> (and I sincerely hope so!) solved a problem for our weekly e-letter
> which has, of late, been munched due to our ISP's smtp server being
> blacklisted and limiting our use of the BCC field for hundreds of
> addresses.
>
> What Direct Mail seems to have is its own built in mail server but
> I presume it is invoking the normally dormant Sendmail code within
> OS X. Is this correct?

Well, now that I've answered my own question instead of yours,
perhaps I should try to answer yours. (Sometimes my idea of the
question being asked gets in the way of listening to the question,
unfortunately. Sorry about that.)

To test this, I temporarily renamed /usr/sbin/sendmail to /usr/sbin/
sendmaix and sent an email with DirectMail to myself same as the
previous one, and it succeeded using the direct mode again. This
indicates that DirectMail does NOT depend on the built-in sendmail
code to accomplish its task. It must have its own implementation of
sendmail's relevant capabilities.

Best regards,

Geoff Odhner
.

ebchi - Jul 25, 2006 10:34 am (#13 Total: 18)  

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Re: Sending newsletters from a Mac

I use Constant Contact (www.constantcontact.com) to send out seasonal newsletters to my clients. There are lovely templates to use and it is simple to include photos and graphics. If your mailing list is fewer than 50, it is free. There is a monthly charge for larger lists.

Edna Brandt Licensed Acupuncturist www.ednabrandt.com

jwblist (apparently) - Jul 26, 2006 10:47 am (#14 Total: 18)  

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Re: Sending newsletters from a Mac

On Jul 25, 2006, at 10:34 AM, Geoffrey Odhner wrote:

> From this header you can see that DirectMail initiated the mailing
> on my local machine, anemone, and sent it directly to
> kelvin.pobox.com, the initial destination, which is a forwarder,
> which forwarded it to my primary account on odhner.net, which is a
> domain hosted on the domain pro60.cedant.com.
>
>
>> What is not clear though, is whether that code, once activated, is
>> creating a security hole that spammers can exploit. That would be
>> like jumping from a hot frying pan right into the fire!
>
> Yes, this approach could facilitate spamming, I'm afraid. It's
> certainly not why I got this software, and I did think twice before
> buying it, because I don't like to support a software vendor who's
> intentions are to support spammers, but since I don't really know his
> intentions, I bought the software I need. On the other hand, if
> you're asking whether this creates a hole in *your* system that
> spammers can exploit, then I really don't think so. It's just like
> any other program you run that initiates a connection to the outside
> world. Unless you have an existing hole already, this should make no
> difference to your security.


It connected outward directly, without using a local sendmail or
postfix. There's no reason to believe it used a mail command, rather
than SMTP code built in (SMTP is trivial for simple sending).

Try sending to an invalid address at pobox.com. See whether it warns
you about the invalidity. Try sending to someplace which does
greylisting (and where your current IP/sending address/recipient
address are unknown); see what it does about the 4xx error associated
with the greylisting. If it queues and tries again, that means it's
doing some of the harder part of SMTP sending (it probably is).

But the real issue with respect to your turning into a relayer of
spam is whether it receives messages from outside. It probably does
not, because
   a. it has no reason to (bounces after acceptance will use your
regular incoming mail path)
   b. Verizon may or may not forward port 25 to your gateway
   c. unless you have an unusual home setup, your gateway wouldn't
send port 25 connections to your machine anyhow.

Test: Have DirectMail running and execute in Terminal the command
netstat -nv
You'll see lines like
Proto Recv-Q Send-Q Local Address Foreign Address
(state)
...
tcp4 0 0 127.0.0.1.1033 127.0.0.1.1015
ESTABLISHED
...
(And some more for udp4, which you can ignore.

The ones you care about are the ones with your machine's LAN IP
address (which I removed for my machine in the above). The number
after the 127.0.0.1 IP address above is the port being listened to
(1033 is "netinfo-local"). (Or leave the -n out of the command, and
*some* of the port numbers will be translated to service names
("netinfo-loca" above--as truncated).

Further test, if your machine IS listening on port 25: check your
current public IP (eg, with http://www.showmyip.com --ignore the
sales pitch) then, from another, non-Verizon machine, telnet to that
IP at port 25 (or have a friend do so)--you're hoping to see the
connection refused (or time out).

My guess is that you are in no danger of relaying without working
hard to do so. (If your machine runs a web server visible to the
world with PHP forms which do mailing, you're in much greater danger.)

This part of the first pobox Received: header
      Received: from anemone.local
is bad news...as you can see later, that earned you a spam score:
FORGED_RCVD_HELO
(the text anemone.local is syntactically correct, and true, but
"impossible" as the public name of a machine, hence "forged").

Try executing, in Terminal (as an admin user, although that and the
sudo are probably overkill) assuming the bash shell
HOSTNAME=pool-70-104-90-61.pskn.east.verizon.net
before you retry your test. (Use your then-current name for your
then-current IP.) You should see the FORGED_RCVD_HELO go away, and
the spam score decrease. The HTML_SHORT_LENGTH will likely go away
for the real newsletter (just as well, because the real newsletter
will no doubt get other points).

This part of the spam testing: MPART_ALT_DIFF is also bad news...it
seems to say that the plain text part of the message doesn't match
the HTML part. Spam points.

Some sites are likely to give spam points for
X-Mailer: Direct Mail for Mac OS X
or to score the other things differently, or both. You're getting 1.8
+ points already, even with the negative points for passing SPF as
Verizon saw it (I don't know how Verizon scores that--the as-shipped
SpamAssassin gives each of those two passes a very small negative
score as sort of a place holder. (You passed SPF because pobox.com
took care of that for you--that's why the
Return-Path: <SRS0=cjSb=BK=Franklin.com=Geoff_Odhner@bounce2.pobox.com>
is what it is. The address pobox.com would use to send along a
bounce to you is encoded into that local part along with magic which
validates the address (for a while).

Bottom line is that some of your recipients will get the message and
some won't. But that's normal for mailing lists, unfortunately
(thanks, spammers). But it's certainly worth a try (and if your
recipients have the sending address you use for the newsletter
whitelisted at their provider and/or present in their address book,
they have a better chance of receiving the messages). Your AOL
recipients will probably NOT receive your messages, and you won't get
bounces to say so.

All in all, DirectMail indeed looks useful for your purpose.
(Anything that sends directly will have the same problem with AOL.)

   --John


netman - Jul 26, 2006 10:47 am (#15 Total: 18)  

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Re: Sending newsletters from a Mac

Hi folks,

though it doesn't seem to be a real issue here, I'd like to mention that I have used MaxBulk and DirectMail and they both ran into problems with recipient lists more than say 15,000 addresses. Sometimes things worked fine, sometimes they didn't (programme crashes), which was pretty dissatisfying, especially as I have to send out a monthly newsletter to some 35,000 addresses.

After a lot of searching the only programme I found that could handle those large numbers without problems was IntelliMerge which admittedly is the most expensive one and it has a number of "annoying habits" like not remembering window sizes and positions, no scroll wheel support and some more. But the support team is very nice and quick to respond. I hope they'll change some of the things I mentioned with the next update.

Anyway, just wanted to mention the problem with large lists, because it can be pretty annoying to get one programme and then another and yet another because they all have some shortcomings. And most trial versions don't allow a test shot with more than 25 recipients.

Best regards

Thilo Dannenmann

John_Wolff - Jul 26, 2006 11:39 pm (#16 Total: 18)  

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Re: Sending newsletters from a Mac

On Jul 25, 2006 Geoff.Odhner wrote:

This indicates that DirectMail does NOT depend on the built-in sendmail code to accomplish its task. It must have its own implementation of sendmail's relevant capabilities.


Many thanks Geoff and John for your detailed testing. Geoff's conclusion is supported by a reply I got back from Jonathon Hammer, the author of Direct Mail;

Direct Mail doesn't use the Sendmail code, so there is no danger of your machine being opened up to spammers. Direct mode doesn't start any server services on your machine, so it's 100% safe.


After the fiasco we've been through over these last two weeks and Thilo's cautionary advice, we're going to try Direct Mail this week and keep our options open with our Web Designer's own package which they call Fan Mail. We never realised we were sitting so close to the bleeding edge of this technology!

Many thanks again for all the enlightenment and shared knowledge that TidBITS make available.

Cheers,

John Wolff Hamilton, NZ

Jerry Nilson - Aug 15, 2006 12:30 pm (#17 Total: 18)  

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Re: Sending newsletters from a Mac

Or become and ISP yourself! ;-) /Jerry

nico235 - Sep 5, 2006 10:03 am (#18 Total: 18)  

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Re: Sending newsletters from a Mac

I have used Emerge (mentioned by Michael) for some years, and while I like it as an application it has never been properly fixed for OS X, and has many problems with displaying text properly. I have been in touch with Galleon (the developers) in the last year and they say the product is still being supported/developed -- but you wouldn't guess this from their site: http://www.galleon.com/emerge/

More generally, there are a number of factors that need to be considered in this discussion:

  • Effectiveness for bulk mailing
  • Ability to customise messages (something Emerge is good for)
  • Integration with existing address book or database
  • Ability to customise for reply-to, etc, and to manage bounces



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