Outlook 2007 junk mail in cached mode odd problem

  • Thread starter banks1850@gmail.com
  • Start date Views 2,457
B

banks1850@gmail.com

This is a complex one. We have 2 domains, 1 for our application (asp)

sending cdosys emails to clients through postfix (works fine) and our

corporate domain. They are completely separate with separate gateways

and external ips. When we send an email to anyone using Outlook 2007

as a client with cached mode turned on and set to high (the way

outlook comes out of the box), it goes directly to junk mail. At

first I thought this was a DNS issue, nope. then I thought it was an

issue with our mail headers (our internal machines add header entries

with their internal IP address to the email) but then I removed those

entries at the postfix server, still the same problem), so I played

with the email iteself, scored it with some testing software, and it

comes up clean as a whistle (it also passes our corporate spam filter

no problem).

So In desparation, I connected directly to exchange as the smtp out to

send the email, and voila, it still goes to junk, no spam filtering,

no relays, no nothing, just a plain old cdosys message with a to,

from, subject, body, and smtp server and port. I know the sender

email address is listed in our exchange, but the email still goes

directly to junk. Can anyone think of a reason why this is

happening? I am so supremely frustrated with this. Any other client

(including Outlook 2003 with spam filtering turned on and set to high)

works fine, it's just Outlook 2007. and yes, I have tried both the

original spam filters that come installed, and the latest downloaded

filters from microsoft. I put in a ticket with MS, but of course,

they say they can't help because their spam filters are proprietary

and they can't tell me what the blocking reason is because that would

allow "possible spammers" to format their emails to bypass their junk

filters. Give me a break!

Please if anyone knows what I can do to help, I'm all ears, this is

making me age pre-maturely!
 
L

Lanwench [MVP - Exchange]

banks1850@gmail.com wrote:
> This is a complex one. We have 2 domains, 1 for our application (asp)
> sending cdosys emails to clients through postfix (works fine) and our
> corporate domain. They are completely separate with separate gateways
> and external ips. When we send an email to anyone using Outlook 2007
> as a client with cached mode turned on and set to high (the way
> outlook comes out of the box), it goes directly to junk mail. At
> first I thought this was a DNS issue, nope. then I thought it was an
> issue with our mail headers (our internal machines add header entries
> with their internal IP address to the email) but then I removed those
> entries at the postfix server, still the same problem), so I played
> with the email iteself, scored it with some testing software, and it
> comes up clean as a whistle (it also passes our corporate spam filter
> no problem).

> So In desparation, I connected directly to exchange as the smtp out to
> send the email, and voila, it still goes to junk, no spam filtering,
> no relays, no nothing, just a plain old cdosys message with a to,
> from, subject, body, and smtp server and port. I know the sender
> email address is listed in our exchange, but the email still goes
> directly to junk. Can anyone think of a reason why this is
> happening? I am so supremely frustrated with this. Any other client
> (including Outlook 2003 with spam filtering turned on and set to high)
> works fine, it's just Outlook 2007. and yes, I have tried both the
> original spam filters that come installed, and the latest downloaded
> filters from microsoft. I put in a ticket with MS, but of course,
> they say they can't help because their spam filters are proprietary
> and they can't tell me what the blocking reason is because that would
> allow "possible spammers" to format their emails to bypass their junk
> filters. Give me a break!

> Please if anyone knows what I can do to help, I'm all ears, this is
> making me age pre-maturely!


If you turn off the junk email filtering in OL2007 entirely what happens?

You mention cached mode, but does the same thing happen when working online?
 
B

banks1850@gmail.com

On May 7, 8:14 am, "Lanwench [MVP - Exchange]"

<lanwe...@heybuddy.donotsendme.unsolicitedmailatyahoo.com> wrote:
> banks1...@gmail.com wrote:
> > This is a complex one.  We have 2 domains, 1 for our application (asp)
> > sending cdosys emails to clients through postfix (works fine) and our
> > corporate domain.  They are completely separate with separate gateways
> > and external ips.  When we send an email to anyone using Outlook 2007
> > as a client with cached mode turned on and set to high (the way
> > outlook comes out of the box), it goes directly to junk mail.  At
> > first I thought this was a DNS issue, nope.  then I thought it was an
> > issue with our mail headers (our internal machines add header entries
> > with their internal IP address to the email) but then I removed those
> > entries at the postfix server, still the same problem), so I played
> > with the email iteself, scored it with some testing software, and it
> > comes up clean as a whistle (it also passes our corporate spam filter
> > no problem).

>
> > So In desparation, I connected directly to exchange as the smtp out to
> > send the email, and voila, it still goes to junk, no spam filtering,
> > no relays, no nothing, just a plain old cdosys message with a to,
> > from, subject, body, and smtp server and port.  I know the sender
> > email address is listed in our exchange, but the email still goes
> > directly to junk.  Can anyone think of a reason why this is
> > happening?  I am so supremely frustrated with this.  Any other client
> > (including Outlook 2003 with spam filtering turned on and set to high)
> > works fine, it's just Outlook 2007.  and yes, I have tried both the
> > original spam filters that come installed, and the latest downloaded
> > filters from microsoft.  I put in a ticket with MS, but of course,
> > they say they can't help because their spam filters are proprietary
> > and they can't tell me what the blocking reason is because that would
> > allow "possible spammers" to format their emails to bypass their junk
> > filters.  Give me a break!

>
> > Please if anyone knows what I can do to help, I'm all ears, this is
> > making me age pre-maturely!


> If you turn off the junk email filtering in OL2007 entirely what happens?
> You mention cached mode, but does the same thing happen when working online?-



No, it's only in cached mode. Outlook Junk mail doesn't work when

working online (that's a "feature" from microsoft). Or more

specifically, the junk filter uses the server's junk lists, which are

from exchange 2003 and don't flag this email. Obviously one of the

filtering parameters in the new Outlook junk mail settings flag this,

but I don't know what it is, and microsoft won't (I stress, I have

asked, they WON'T) work with me on this, even though this is purely an

internal issue. I have picked this email to the bone, there's NOTHING

in it anymore, yet it still filters to junk.
 
L

Lanwench [MVP - Exchange]

banks1850@gmail.com wrote:
> On May 7, 8:14 am, "Lanwench [MVP - Exchange]"
> <lanwe...@heybuddy.donotsendme.unsolicitedmailatyahoo.com> wrote:
> > banks1...@gmail.com wrote:
> >> This is a complex one. We have 2 domains, 1 for our application
> >> (asp) sending cdosys emails to clients through postfix (works fine)
> >> and our corporate domain. They are completely separate with
> >> separate gateways and external ips. When we send an email to anyone
> >> using Outlook 2007 as a client with cached mode turned on and set
> >> to high (the way outlook comes out of the box), it goes directly to
> >> junk mail. At first I thought this was a DNS issue, nope. then I
> >> thought it was an issue with our mail headers (our internal
> >> machines add header entries with their internal IP address to the
> >> email) but then I removed those entries at the postfix server,
> >> still the same problem), so I played with the email iteself, scored
> >> it with some testing software, and it comes up clean as a whistle
> >> (it also passes our corporate spam filter no problem).

> >
> >> So In desparation, I connected directly to exchange as the smtp out
> >> to send the email, and voila, it still goes to junk, no spam
> >> filtering, no relays, no nothing, just a plain old cdosys message
> >> with a to, from, subject, body, and smtp server and port. I know
> >> the sender email address is listed in our exchange, but the email
> >> still goes directly to junk. Can anyone think of a reason why this
> >> is
> >> happening? I am so supremely frustrated with this. Any other client
> >> (including Outlook 2003 with spam filtering turned on and set to
> >> high) works fine, it's just Outlook 2007. and yes, I have tried
> >> both the original spam filters that come installed, and the latest
> >> downloaded filters from microsoft. I put in a ticket with MS, but
> >> of course, they say they can't help because their spam filters are
> >> proprietary and they can't tell me what the blocking reason is
> >> because that would allow "possible spammers" to format their emails
> >> to bypass their junk filters. Give me a break!

> >
> >> Please if anyone knows what I can do to help, I'm all ears, this is
> >> making me age pre-maturely!

>

>> If you turn off the junk email filtering in OL2007 entirely what
> > happens?
> > You mention cached mode, but does the same thing happen when working
> > online?-

>

>


> No, it's only in cached mode. Outlook Junk mail doesn't work when
> working online (that's a "feature" from microsoft). Or more
> specifically, the junk filter uses the server's junk lists, which are
> from exchange 2003 and don't flag this email. Obviously one of the
> filtering parameters in the new Outlook junk mail settings flag this,
> but I don't know what it is, and microsoft won't (I stress, I have
> asked, they WON'T) work with me on this, even though this is purely an
> internal issue. I have picked this email to the bone, there's NOTHING
> in it anymore, yet it still filters to junk.


Ahah. Well, to be honest, I'd recommend turning off the icky Outlook

junkmail filter. I've never been fond of it to begin with - what's the

reason you need it, if you've got external filtering? If your users want to

use it, well, train them to add it to safe senders.
 
B

banks1850@gmail.com

On May 7, 10:07 am, "Lanwench [MVP - Exchange]"

<lanwe...@heybuddy.donotsendme.unsolicitedmailatyahoo.com> wrote:
> banks1...@gmail.com wrote:
> > On May 7, 8:14 am, "Lanwench [MVP - Exchange]"
> > <lanwe...@heybuddy.donotsendme.unsolicitedmailatyahoo.com> wrote:
> >> banks1...@gmail.com wrote:
> >>> This is a complex one. We have 2 domains, 1 for our application
> >>> (asp) sending cdosys emails to clients through postfix (works fine)
> >>> and our corporate domain. They are completely separate with
> >>> separate gateways and external ips. When we send an email to anyone
> >>> using Outlook 2007 as a client with cached mode turned on and set
> >>> to high (the way outlook comes out of the box), it goes directly to
> >>> junk mail. At first I thought this was a DNS issue, nope. then I
> >>> thought it was an issue with our mail headers (our internal
> >>> machines add header entries with their internal IP address to the
> >>> email) but then I removed those entries at the postfix server,
> >>> still the same problem), so I played with the email iteself, scored
> >>> it with some testing software, and it comes up clean as a whistle
> >>> (it also passes our corporate spam filter no problem).

>
> >>> So In desparation, I connected directly to exchange as the smtp out
> >>> to send the email, and voila, it still goes to junk, no spam
> >>> filtering, no relays, no nothing, just a plain old cdosys message
> >>> with a to, from, subject, body, and smtp server and port. I know
> >>> the sender email address is listed in our exchange, but the email
> >>> still goes directly to junk. Can anyone think of a reason why this
> >>> is
> >>> happening? I am so supremely frustrated with this. Any other client
> >>> (including Outlook 2003 with spam filtering turned on and set to
> >>> high) works fine, it's just Outlook 2007. and yes, I have tried
> >>> both the original spam filters that come installed, and the latest
> >>> downloaded filters from microsoft. I put in a ticket with MS, but
> >>> of course, they say they can't help because their spam filters are
> >>> proprietary and they can't tell me what the blocking reason is
> >>> because that would allow "possible spammers" to format their emails
> >>> to bypass their junk filters. Give me a break!

>
> >>> Please if anyone knows what I can do to help, I'm all ears, this is
> >>> making me age pre-maturely!

>
> >> If you turn off the junk email filtering in OL2007 entirely what
> >> happens?
> >> You mention cached mode, but does the same thing happen when working
> >> online?-

>
> >

>
> > No, it's only in cached mode.  Outlook Junk mail doesn't work when
> > working online (that's a "feature" from microsoft).  Or more
> > specifically, the junk filter uses the server's junk lists, which are
> > from exchange 2003 and don't flag this email.  Obviously one of the
> > filtering parameters in the new Outlook junk mail settings flag this,
> > but I don't know what it is, and microsoft won't (I stress, I have
> > asked, they WON'T) work with me on this, even though this is purely an
> > internal issue.  I have picked this email to the bone, there's NOTHING
> > in it anymore, yet it still filters to junk.


> Ahah. Well, to be honest, I'd recommend turning off the icky Outlook
> junkmail filter. I've never been fond of it to begin with - what's the
> reason you need it, if you've got external filtering? If your users want to
> use it, well, train them to add it to safe senders.-



It's not a question of turning it on or off. The application sends

email to clients, we can't tell them to turn off their Outlook Junk

mail filters, we can only do our best to make sure that mail sent to

them doesn't filter to junk. And since it's automated and sends mail

to NEW clients, we don't even have a relationship with them to inform

them of the possibility.
 
L

Lanwench [MVP - Exchange]

banks1850@gmail.com wrote:

\

<snip>
> It's not a question of turning it on or off. The application sends
> email to clients, we can't tell them to turn off their Outlook Junk
> mail filters, we can only do our best to make sure that mail sent to
> them doesn't filter to junk. And since it's automated and sends mail
> to NEW clients, we don't even have a relationship with them to inform
> them of the possibility.


Ah. Well - I'm really not sure what to tell you. You might try the Outlook

group for more help - this is an Outlook issue.

And if your clients are signing up for the mail on a webpage, you might tell

them to whitelist sender blah@blah.com in whatever junkmail management

product they use. It's really up to the recipient at that point. Sorry I

don't have anything more helpful to add - if Microsoft ain't helping, I'm

not sure any of us out in the trenches could do more.
 

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