Unable to send contents of inbox?

[(PeteCresswell)]

My usual mail client is Forte's "Agent".

But I want to do a mass mailing without multiple addresses in BCC, so I
went the MS Word Mail/Merge route.

My test successfully left documents in Outlook 2003's OutBox, but I
cannot get Outlook to send them.

Tools | E-Mail Accounts | ....| "Test Account Settings" returns success
for all the outgoing server tests. The incoming mail server tests are
not successful - and that's the way I'd like to keep it (not wanting
Outlook to siphon all my incoming emails from the server before Agent
can get to them).

Is the incoming issue a probable cause for not being able to send those
messages from the OutBox?

Something else to look for?

 

[VanguardLH]

My usual mail client is Forte's "Agent".

But I want to do a mass mailing without multiple addresses in BCC, so I
went the MS Word Mail/Merge route.

That means you want all the recipients' e-mail addresses divulged in
the To/Cc headers. That is very rude because you are telling every
recipient the e-mail addresses of all other recipients. It is highly
UNlikely that you have permission from all those recipients to let you
publicize their e-mail addresses to anyone else.

My test successfully left documents in Outlook 2003's OutBox, but I
cannot get Outlook to send them.

Was Outlook actually running when you ran the mailmerge operation?
Calls to Outlook to generate outbound e-mails when Outlook is not
actually loaded only load a stub of Outlook that is sufficient to
compose the new messages and deposit them in its Outbox folder. That
will not send those messages because Outlook wasn't load. The stub
loads, does its work to create the messages, and then Outlook unloads.
That means Outlook isn't around to do the sending afterward. Make
sure Outlook is loaded when you do the mailmerge operation so it
remains loaded afterward to do its sending.

You should also check if Outlook is configured to send. Maybe it's
configured to NOT send automatically and instead will only send when
the user initiates a manual send operation. You need to configure
Outlook (assuming it is loaded before and remains loaded after the
mailmerge operation) to automatically send e-mails. Then when Outlook
sees the event of a new item deposited into its Outbox folder it will
initiate an automatic send. If items are dropped into the Outbox
folder while Outlook is not loaded (i.e., load a stub of Outlook to
compose the e-mail but Outlook unloads afterward), Outlook will not
see that event (since it doesn't happen) when you next load Outlook.
It will see a bunch of items in its Outbox folder but there is no
event to put them there while that instance of Outlook is running.

Drag the items sitting in the Outbox to your Drafts folder. Now send
each one. If you don't want to resend all those messages, redo your
mailmerge operation but make sure Outlook was loaded first.

Is the version of Outlook you use (where the messages are stuck in its
Outbox folder) the SAME version as Word where you started the
mailmerge operation? For integration features to work means the
versions of the Office components involved must be the same.

Tools | E-Mail Accounts | ....| "Test Account Settings" returns success
for all the outgoing server tests. The incoming mail server tests are
not successful - and that's the way I'd like to keep it (not wanting
Outlook to siphon all my incoming emails from the server before Agent
can get to them).

Is the incoming issue a probable cause for not being able to send those
messages from the OutBox?

Something else to look for?

Outlook only needs an Exchange or SMTP account defined within it to
*send* e-mails. Receive setup is irrelevant. You don't indicate if
you defined bogus inbound e-mail servers in Outlook or edited the
send/receive group(s) to leave enabled the send function but disabled
the receive function. Also, since you mention Outlook is not
configured to receive then maybe you configured Outlook to
automatically poll your accounts -- and that's needed for Outlook to
send when the new-item-in-Outbox event happens in Outlook.

How many recipients per message does your e-mail provider allow? You
might want to send to a million recipients but your e-mail provider
only grants you a max of 25 or 50 recipients per message. With
mailmerge, you should be sending one message to one recipient, not one
message to many recipients. In that case, you can still run afoul of
spam abuse quotas at your e-mail provider. They may restrict how many
messages you can send per minute as well as how many mail sessions you
can establish in some time frame or how far apart each mail session
must be. Mailmerge cannot be configured to accommodate anti-spam
quotas at e-mail providers. Mailmerge want to send out the messages
as soon as they are created (i.e., as soon as Outlook, when running,
sees the new-item event for its Outbox folder). You cannot regulate
how many messages (thus how many recipients) are sent within one mail
session or how long to wait until the next mail session. Say you sent
100 e-mails (one each to a one recipient). Are there 100 e-mails
lingering in the Outbox folder or are there less, like 20 got sent and
80 are still sitting there? To accomodate the anti-spam, anti-abuse
quotas for a personal-use e-mail account, you will need to look at
using a mass mailing program that lets you configure max messages per
N minutes and how long to wait between mail sessions. If you want to
continue using Office's unmetered mailmerge function, you'll have to
get a business-class e-mail account with much small or no anti-spam
and anti-abuse quotas.

 

[(PeteCresswell)]

Per (PeteCresswell):

Is the incoming issue a probable cause for not being able to send those
messages from the OutBox?

Update: I have both servers config'd so that they pass Outlook's test.

But now, when I initiate a mail-merge from Word, something seems tb
hanging. Word has an endless hourglass and Outlook becomes
unresponsive.

??

 

[(PeteCresswell)]

Per VanguardLH:

That means you want all the recipients' e-mail addresses divulged in
the To/Cc headers. That is very rude because you are telling every
recipient the e-mail addresses of all other recipients. It is highly
UNlikely that you have permission from all those recipients to let you
publicize their e-mail addresses to anyone else.

No. That's why the mail-merge. It boogies though a list of addresses
and sends one email to each address.... no other addresses except my own
return address are divulged.

I was going to use BCC, but somebody advised me that spam filters tend
to block messages with too many BCC entries.

 

[(PeteCresswell)]

Per VanguardLH:

Was Outlook actually running when you ran the mailmerge operation?

Yes.. but it's starting to look like a moving target.

I just had a successful test using the "HTML" option.

Then I figured I'd try it again using plain text.... and Word hung -
eternal hourglass. I killed Word, tried again with HTML, and same
thing: Word is hung. But now Outlook 2003 continues to be responsive.

You need to configure
Outlook (assuming it is loaded before and remains loaded after the
mailmerge operation) to automatically send e-mails.

The only setting I could find specified how often to automatically
invoke Send/Receive. It was set to 5 minutes and I reduced it to 1
minute just on GPs.... But I'm still back to Word's eternal hourglass.

Is the version of Outlook you use (where the messages are stuck in its
Outbox folder) the SAME version as Word where you started the
mailmerge operation?

I think so: Word 2003, Outlook 2003.

Outlook only needs an Exchange or SMTP account defined within it to
*send* e-mails. Receive setup is irrelevant. You don't indicate if
you defined bogus inbound e-mail servers in Outlook or edited the
send/receive group(s) to leave enabled the send function but disabled
the receive function. Also, since you mention Outlook is not
configured to receive then maybe you configured Outlook to
automatically poll your accounts -- and that's needed for Outlook to
send when the new-item-in-Outbox event happens in Outlook.

I wimped out on that one and now Outlook is correctly config'd to both
send and receive.

How many recipients per message does your e-mail provider allow? You
might want to send to a million recipients but your e-mail provider
only grants you a max of 25 or 50 recipients per message.

My test has 3 recipients. The final "Production" run will have 132.

With

mailmerge, you should be sending one message to one recipient, not one
message to many recipients.

That is what I'm doing.... at least I *hope* that's what I'm doing...

 

[(PeteCresswell)]

Per (PeteCresswell):

Something else to look for?

Well, I just got two tests in a row to run... and also managed to mail
the document in question to five committee members for approval before
sending it to the 132 final recipients.

All I can think of is that there's something weird going on with my
Windows XP.

It's not like this is going to become a daily task... maybe a half-dozen
iterations over the next six months and that'll be it....

That being the case, as long as I can stumble though the process
successfully even with 2 out of three tries failing, I'd call it "Case
Closed".

 

[VanguardLH]

Per VanguardLH:


No. That's why the mail-merge. It boogies though a list of addresses
and sends one email to each address.... no other addresses except my own
return address are divulged.

I was going to use BCC, but somebody advised me that spam filters tend
to block messages with too many BCC entries.

There is *no* BCC header in any received e-mail. The only place you
will see "Bcc" is in your e-mail client. That is a field, not a
header in the sent e-mail. Your e-mail client takes all the
recipients in the To, Cc, and Bcc *fields* in the new-mail compose
window and compiles an aggregate list of recipients. When your e-mail
client connects to the server, it sends a *separate* copy to each
recipient using the RCPT-TO command. If you had 10 recipients in the
To field, 5 in the Cc field, and 20 in the Bcc field, your client will
sent 35 RCPT-TO commands to the server, one for each recipient. Your
message will have 10 recipients in the To *header*, 5 in the CC
*header*, and there will be *no* Bcc header.

How spam filters work regarding use of the Bcc header is they see a
received e-mail does specify the recipient's e-mail address in the To
or Cc headers. There is no Bcc header to inspect since it isn't
there. Getting an e-mail that is not addressed to you often means
that e-mail was sent to multiple recipients either using the Bcc
header or via a mass mailing client that merely issues a RCPT-TO
command for each recipient from a list or database. Mailmerge works
differently by placing one recipient in the To header so the anti-spam
filter sees an e-mail has the address specified in the To/Cc headers
for the receiving account. Mass mailing software can do the same but
doesn't have to.

Bcc is a *FIELD* shown in the new-mail compose window in your e-mail
client. There is never a Bcc header in any e-mail that you send.
One, your e-mail client should never add a Bcc header. If it does,
that client is fucked up, has been reconfigured (I don't know of any
that let you include a Bcc header), hacked, or a mass mailing client
was used instead of a regular e-mail client. Two, your sending mail
server should check if there is a Bcc header (in case you are using an
extremely ancient or defective client that adds it). If found, the
sending server should strip out that header. Three, the receiving
server should also strip out any Bcc header if found in a received
e-mail.

You aren't including a Bcc *header* in your outbound e-mails just
because your e-mail client shows you a Bcc *field*. It's a BLIND
carbon copy which means that list of recipients should not appear
anywhere in any header within the e-mail.

If you use the Bcc field (not a header) which generates multiple
RCPT-TO commands to send a copy of your e-mail to each recipient
separately, and because that means the recipient is NOT specified in
any header in your e-mail, the receiving server will see a received
e-mail with the recipient's account specified in the envelope
information (what the servers see, not what is in the e-mail itself)
but with the recipient not specified, they figure it is bulk mail. It
might be spam, might be a newsletter (subscribed or not), or a
personal invitation to a party from a friend. They don't know. They
only know the recipient isn't specified in the headers of the e-mail.
So put something in the headers. Put your own e-mail address in the
To field. If it's a newsletter, add a contact in your e-mail client
named "My newsletter" (or whatever will identify it to your
recipients) with an e-mail address that points back at you (or
whatever reply-to e-mail address you want to use). Then the recipient
gets an e-mail without them specified but the To and Cc headers are
not blank. When using Bcc (which means no recipients are specified),
make sure you do NOT leave blank the To/Cc headers. Blank To/Cc
headers are valid per SMTP specs but can run afoul of anti-spam
filters (which have no specs to follow and are whatever rules the
provider wants to employ).

 

[VanguardLH]

I just had a successful test using the "HTML" option.

Then I figured I'd try it again using plain text.... and Word hung -
eternal hourglass. I killed Word, tried again with HTML, and same
thing: Word is hung. But now Outlook 2003 continues to be responsive.

What add-ons or macros have you installed in Outlook? You could
disable them or run Outlook in its safe mode but you might not use or
need some of those add-ons and should remove them.

For example, installing an anti-virus program often will install its
add-on for use by Outlook although such scanning is superfluous. This
add-on will incur delays. If the AV program inspects the entire
message before it passes it on from the client (Outlook) to the
server, the mail session got established from client to server but the
server waits there for the message during the DATA command.
Eventually the server is going to timeout because it doesn't see any
bytes getting sent. To the server, the client is dead or overly slow.
If the AV program does an on-the-fly inspection where it looks at a
few bytes it buffers up and then sends them to the server, this can
still cause enough of a delay that the server will timeout the mail
session because it is taking too long. That server has a limited
amount of resources to allocate to all the concurrent sessions it
handles for thousands of users. If it sees an extremely slow client,
it has to dump it to provide those limited resources to a better
connection.

The polling of e-mail by an AV program is superfluous. Why? Because
the same engine that scans your e-mails on receive or send is the same
engine that is scanning the files on your host. When receiving
e-mails, the AV incurs a delay on the receive before the bytes can
accrue into a record in the database file for the e-mail client.
However, since the file is getting written on the hard disk, the AV
program will scan that file. When sending e-mails, if the AV didn't
catch a file (that you attach to e-mail) on the hard disk as infected
then it also won't catch the attachment as infected. You get no
higher coverage of detection by having an AV program scan your inbound
or outbound messages. You only change when that detection occurs.
For received e-mails, the AV can spot a string of bytes (signature)
for an infection while it inspects the bytes in the e-mail traffic, so
you get warned a little bit earlier, like a few milliseconds since
those same bytes will write into a file that the AV program scans.
For sending, the AV should've already scanned the file to be attached
when it got opened to get read by the e-mail client so any further
detection would be later, not earlier.

You gain nothing by having AV scan your e-mails. Turn it off or
disable e-mail scanning in your AV program. For some AV programs, all
you have to do is turn it off. For others, turning off the scanning
does not remove their transparent proxy. While there is less delay
because the e-mail traffic is not scanned for malware, the e-mail
traffic still has to pass through their local proxy. If their proxy
is slow or defective or flaky, so will be your e-mail. You have to
uninstall the AV program and during a reinstall use a custom install
procedure to NOT include their e-mail scanner module. Then their
proxy won't be intercepting e-mail traffic between your client and the
server.

The only setting I could find specified how often to automatically
invoke Send/Receive. It was set to 5 minutes and I reduced it to 1
minute just on GPs.... But I'm still back to Word's eternal hourglass.

Actually you do NOT want a short polling interval. For mailmerge, you
want automatic polling enabled. That means when Outlook sees the
event (which means it must be fully loaded) of a new item showing up
in its Outbox that it establishes a mail session to send that new
item.

As for the interval, 1 minute is too fast and can cause problems. For
example, if an existing ongoing mail session has to transfer a new
item to the server but it is a large item (due to body size or
attachments) or the server is slow or your route is slow (there is a
slow node in the route between you and the server), it could take over
1 minute to transfer that new item. With attachments, it could
several minutes to transfer the message. However, if Outlook is
configured to start another mail poll in 1 minute, the current session
still trying to transfer a huge e-mail or to a slow server will get
stomped on. What it was sending will get aborted and that new message
won't get sent. That's because Outlook was told to start a new mail
session so the old one gets aborted and you start another. Yet that
same huge e-mail or slow server will make that session last longer
than a minute and then the next 1-minute mail poll comes along and
quashes the current mail session and you start over again. Even 5
minutes can sometimes be too short because a prior and existing
session can get stepped on. Plus it is unlikely in 5 minutes that you
will read all those numerous e-mails along with composing replies. If
you don't get a lot of e-mails then 5 minutes is too short simply
because you're aren't getting many e-mails piling up on the server in
that time. 1-5 minutes are wasteful and actually abusive to the
server that has to allocates resources to your connection when there
are no new e-mails waiting for you up on the server or because you end
up stepping on your own mail session. Start with 10 minutes.

Setting the mail poll interval to 10 minutes does NOT alter the event
triggering to start a new mail session when a new item gets moved into
Outlook's Outbox folder. So your mailmerge will end up generating
mail sessions as fast as it can shove new items into Outlook's Outbox
folder (providing Outlook is fully loaded so it can follow the new
item event with a mail session). This is where you can get in trouble
with your e-mail provider's anti-spam and anti-abuse quotas,
especially if using a personal-use account. Personal-use accounts
expect levels of usage for, well, personal use. Mailing lists more
than a couple dozen recipients in size isn't considered personal use.
Mailmerge has no means of taking a database or recipient list and
regulating how fast new items are shoved into the Outbox (to comply
with the provider's max sessions per minute quota) or how far between
to run the mail sessions (another anti-abuse/spam quota). You can ask
the e-mail provider what are their quotas but often they won't say
because they don't to let spammers know just how fast they can spew
out from that source.

Because of hitting anti-spam and anti-abuse quotas when sending with a
personal-use account, it is often better to either upclass to a
business-use account (which will cost more money) or use a mass
mailing program - and one where you can configure how many messages to
send per minute and how far apart are the mail sessions. Basically
you configure how many can be sent at a time in a group and the
interval between the groups.

My test has 3 recipients. The final "Production" run will have 132.

Which could easily hit anti-abuse quotas with your current e-mail
provider if you are using a personal-use account. For testing,
however, 3 shouldn't be hitting those quotas, so see what happens when
you get your AV program completely out of the way so it does not
interrogate your e-mail traffic and also doesn't continue passing your
e-mail traffic through a local proxy.

 

[VanguardLH]

Per (PeteCresswell):

Update: I have both servers config'd so that they pass Outlook's test.

But now, when I initiate a mail-merge from Word, something seems tb
hanging. Word has an endless hourglass and Outlook becomes
unresponsive.

??

When you have Outlook running, go into Task Manager to check how many
instances of outlook.exe are concurrently loaded, and the same for
winword.exe. Outlook has a long history of not unloading completely
which leaves behind a stub of code still running in a process that
interferes with later loaded instances of Outlook.

Exit Outlook and then check in Task Manager that there are NO
instances of outlook.exe. It usually takes up to a minute for Outlook
to completely close. Just because its GUI (window) disappears doesn't
mean the program itself has completely unloaded.