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cannot send pdf attachments

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Unread 24-03-2008, 02:24 AM   #1
shirl824
Guest
 
Posts: n/a
cannot send pdf attachments

With Outlook 2002 I can't send email with a pdf attachment. When I attempt,
the email appears to send successfully... there is no error message. But
recipients never receive the email if there is a pdf file attached. I've
tried sending the email to myself, with no success. Have also tried using
gmail, thunderbird and bellsouth webmail... with all of those, the email just
times out.
Help, please!
Thanks!
 
Unread 24-03-2008, 03:23 AM   #2
Diane Poremsky [MVP]
Guest
 
Posts: n/a
Re: cannot send pdf attachments

how large is the file? Do you use an anti-virus or firewall that is
filtering email ports?

--
Diane Poremsky [MVP - Outlook]
Author, Teach Yourself Outlook 2003 in 24 Hours
Need Help with Common Tasks? http://www.outlook-tips.net/beginner/
Outlook 2007: http://www.slipstick.com/outlook/ol2007/

Outlook Tips by email:
dailytips-subscribe-request@lists.outlooktips.net

Outlook Tips: http://www.outlook-tips.net/
Outlook & Exchange Solutions Center: http://www.slipstick.com
Subscribe to Exchange Messaging Outlook newsletter:
EMO-NEWSLETTER-SUBSCRIBE-REQUEST@PEACH.EASE.LSOFT.COM

** Please include your Outlook version, Account type, and Windows Version
when requesting assistance **


"shirl824" <shirl824@discussions.microsoft.com> wrote in message
news:6F3AB900-36EE-44A3-B2D6-6A5E3499AED4@microsoft.com...
> With Outlook 2002 I can't send email with a pdf attachment. When I
> attempt,
> the email appears to send successfully... there is no error message. But
> recipients never receive the email if there is a pdf file attached. I've
> tried sending the email to myself, with no success. Have also tried using
> gmail, thunderbird and bellsouth webmail... with all of those, the email
> just
> times out.
> Help, please!
> Thanks!


 
Unread 24-03-2008, 04:23 AM   #3
shirl824
Guest
 
Posts: n/a
Re: cannot send pdf attachments


I've tried with several different pdf attachments. One example is a document
that is 7.33mb. Have Windows XPHome, ServPk 2. Spy Sweeper and Trend Micro
Antivirus, plus Windows Firewall... can't tell that there is any setting
restricting this type of file attachment.
Thanks
"Diane Poremsky [MVP]" wrote:

> how large is the file? Do you use an anti-virus or firewall that is
> filtering email ports?
>
> --
> Diane Poremsky [MVP - Outlook]
> Author, Teach Yourself Outlook 2003 in 24 Hours
> Need Help with Common Tasks? http://www.outlook-tips.net/beginner/
> Outlook 2007: http://www.slipstick.com/outlook/ol2007/
>
> Outlook Tips by email:
> dailytips-subscribe-request@lists.outlooktips.net
>
> Outlook Tips: http://www.outlook-tips.net/
> Outlook & Exchange Solutions Center: http://www.slipstick.com
> Subscribe to Exchange Messaging Outlook newsletter:
> EMO-NEWSLETTER-SUBSCRIBE-REQUEST@PEACH.EASE.LSOFT.COM
>
> ** Please include your Outlook version, Account type, and Windows Version
> when requesting assistance **
>
>
> "shirl824" <shirl824@discussions.microsoft.com> wrote in message
> news:6F3AB900-36EE-44A3-B2D6-6A5E3499AED4@microsoft.com...
> > With Outlook 2002 I can't send email with a pdf attachment. When I
> > attempt,
> > the email appears to send successfully... there is no error message. But
> > recipients never receive the email if there is a pdf file attached. I've
> > tried sending the email to myself, with no success. Have also tried using
> > gmail, thunderbird and bellsouth webmail... with all of those, the email
> > just
> > times out.
> > Help, please!
> > Thanks!

>

 
Unread 24-03-2008, 05:19 AM   #4
F.H. Muffman
Guest
 
Posts: n/a
Re: cannot send pdf attachments

>>> With Outlook 2002 I can't send email with a pdf attachment. When I
>>> attempt, the email appears to send successfully... there is no
>>> error message. But recipients never receive the email if there is a
>>> pdf file attached. I've tried sending the email to myself,
>>> with no success. Have also tried using gmail, thunderbird and
>>> bellsouth webmail... with all of those, the email just times out.

>>
>> how large is the file? Do you use an anti-virus or firewall that is
>> filtering email ports?

>
> I've tried with several different pdf attachments. One example is a document
> that is 7.33mb. Have Windows XPHome, ServPk 2. Spy Sweeper and Trend
> Micro Antivirus, plus Windows Firewall... can't tell that there is any
> setting restricting this type of file attachment.


Easy way to tell.

Create a small text file, like, say, one that only has 'this is a test' in
it.
Rename the file to have an pdf extension.
Try to mail that.

But wait, when you said you get the same problem with bellsouth webmail,
do you mean sending to or sending from? I mean, if you're failing to send
from a web based reader and it's timing out, then it surely isn't an Outlook
issue.
--
-f.h.


 
Unread 24-03-2008, 08:16 AM   #5
VanguardLH
Guest
 
Posts: n/a
Re: cannot send pdf attachments

"shirl824" <shirl824@discussions.microsoft.com> wrote in message
news:6DF545B5-DAE0-4375-BC54-BDF9DD9F4F88@microsoft.com...
>
> I've tried with several different pdf attachments. One example is a
> document
> that is 7.33mb. Have Windows XPHome, ServPk 2. Spy Sweeper and Trend
> Micro
> Antivirus, plus Windows Firewall... can't tell that there is any
> setting
> restricting this type of file attachment.



A 7MB file (based on its size on the hard disk) will mushroom to maybe
50% its original size when it gets encoded into text to put into a MIME
part within the body of your e-mail. Attachments don't go floating out
into the ether somehow separate of your e-mail. They are *in* the body
of your message. All e-mail gets sent as text but encoding can be used
for HTML or binary content. Changing a binary file into an encoded text
section within the body of your message will significantly increase the
size of your message. E-mail was never designed to be a substitute for
file transferring schemes, like FTP. Your 7.33MB file will probably
mushroom to 11MB which might exceed the per-message maximum allowed by
your e-mail provider in your account or exceed the maximum message size
that can be received by the recipient.

Also, spammers have been using .pdf attachments to hide their spam
content from anti-spam filters (because they won't go decoding the
encoded MIME part to then dig inside the .pdf file to see if it is spam,
especially since the content of the .pdf file could be an image instead
of text, and PDF is not a text file, anyway). So maybe the recipient's
anti-spam filters don't like .pdf attachments because they can't check
if it contains spam. Try changing the extension from .pdf to .pdx or
..pxx, attach it, and see if the recipient gets the e-mail (after you
reduce the message size as noted above); if so, they can save the
attachment and rename the extension during the save to .pdf to use that
filetype association on their host.

You could try zipping up the .pdf file to wrap it inside a .zip file and
send it that way to see if the recipient then gets your message.

 
Unread 24-03-2008, 01:22 PM   #6
shirl824
Guest
 
Posts: n/a
Re: cannot send pdf attachments


Ok, I just successfully sent one to myself that was a 770kp file. Is there a
way to determine what size is the limit (other than just sending trials of
various size files)? So if I need to send a larger file, I should try
zipping into a .zip file?
Thanks!
"VanguardLH" wrote:

> "shirl824" <shirl824@discussions.microsoft.com> wrote in message
> news:6DF545B5-DAE0-4375-BC54-BDF9DD9F4F88@microsoft.com...
> >
> > I've tried with several different pdf attachments. One example is a
> > document
> > that is 7.33mb. Have Windows XPHome, ServPk 2. Spy Sweeper and Trend
> > Micro
> > Antivirus, plus Windows Firewall... can't tell that there is any
> > setting
> > restricting this type of file attachment.

>
>
> A 7MB file (based on its size on the hard disk) will mushroom to maybe
> 50% its original size when it gets encoded into text to put into a MIME
> part within the body of your e-mail. Attachments don't go floating out
> into the ether somehow separate of your e-mail. They are *in* the body
> of your message. All e-mail gets sent as text but encoding can be used
> for HTML or binary content. Changing a binary file into an encoded text
> section within the body of your message will significantly increase the
> size of your message. E-mail was never designed to be a substitute for
> file transferring schemes, like FTP. Your 7.33MB file will probably
> mushroom to 11MB which might exceed the per-message maximum allowed by
> your e-mail provider in your account or exceed the maximum message size
> that can be received by the recipient.
>
> Also, spammers have been using .pdf attachments to hide their spam
> content from anti-spam filters (because they won't go decoding the
> encoded MIME part to then dig inside the .pdf file to see if it is spam,
> especially since the content of the .pdf file could be an image instead
> of text, and PDF is not a text file, anyway). So maybe the recipient's
> anti-spam filters don't like .pdf attachments because they can't check
> if it contains spam. Try changing the extension from .pdf to .pdx or
> ..pxx, attach it, and see if the recipient gets the e-mail (after you
> reduce the message size as noted above); if so, they can save the
> attachment and rename the extension during the save to .pdf to use that
> filetype association on their host.
>
> You could try zipping up the .pdf file to wrap it inside a .zip file and
> send it that way to see if the recipient then gets your message.
>
>

 
Unread 24-03-2008, 02:25 PM   #7
VanguardLH
Guest
 
Posts: n/a
Re: cannot send pdf attachments

"shirl824" wrote in message
news:A8E042F7-C9FF-4600-87EB-C6D44C649321@microsoft.com...
>
> "VanguardLH" wrote:
>
>> "shirl824" wrote ...
>> >
>> > I've tried with several different pdf attachments. One example is a
>> > document
>> > that is 7.33mb. Have Windows XPHome, ServPk 2. Spy Sweeper and
>> > Trend
>> > Micro
>> > Antivirus, plus Windows Firewall... can't tell that there is any
>> > setting
>> > restricting this type of file attachment.

>>
>> A 7MB file (based on its size on the hard disk) will mushroom to
>> maybe
>> 50% its original size when it gets encoded into text to put into a
>> MIME
>> part within the body of your e-mail. Attachments don't go floating
>> out
>> into the ether somehow separate of your e-mail. They are *in* the
>> body
>> of your message. All e-mail gets sent as text but encoding can be
>> used
>> for HTML or binary content. Changing a binary file into an encoded
>> text
>> section within the body of your message will significantly increase
>> the
>> size of your message. E-mail was never designed to be a substitute
>> for
>> file transferring schemes, like FTP. Your 7.33MB file will probably
>> mushroom to 11MB which might exceed the per-message maximum allowed
>> by
>> your e-mail provider in your account or exceed the maximum message
>> size
>> that can be received by the recipient.
>>
>> Also, spammers have been using .pdf attachments to hide their spam
>> content from anti-spam filters (because they won't go decoding the
>> encoded MIME part to then dig inside the .pdf file to see if it is
>> spam,
>> especially since the content of the .pdf file could be an image
>> instead
>> of text, and PDF is not a text file, anyway). So maybe the
>> recipient's
>> anti-spam filters don't like .pdf attachments because they can't
>> check
>> if it contains spam. Try changing the extension from .pdf to .pdx or
>> .pxx, attach it, and see if the recipient gets the e-mail (after you
>> reduce the message size as noted above); if so, they can save the
>> attachment and rename the extension during the save to .pdf to use
>> that
>> filetype association on their host.
>>
>> You could try zipping up the .pdf file to wrap it inside a .zip file
>> and
>> send it that way to see if the recipient then gets your message.

>
> Ok, I just successfully sent one to myself that was a 770kp file. Is
> there a
> way to determine what size is the limit (other than just sending
> trials of
> various size files)? So if I need to send a larger file, I should try
> zipping into a .zip file?


You can call your own ISP or whomever is your e-mail provider to ask
them what is the maximum size of an e-mail that you can send, or you
could read their web help pages. You won't know what is the maximum
message size restriction for recipients. Keep the total size (what you
actually send) to under 10MB as most recipients have this as a maximum
message size. If you just write an e-mail, it would be pretty difficult
to be so verbose as to eat up 10MB in text. If you compose in HTML, you
will slightly more than double the size of your e-mail because there
will be a MIME part for the HTML encoded copy and another MIME part for
a plain-text version of your message but, still, it would be pretty hard
to write up a 5MB e-mail. Most e-mails that you hand write will be
under 50KB in size.

It is when you add attachments, especially binary attachments (of which
..pdf is one) that you can exceed the maximum message size. E-mail was
NOT designed to be a file transfer protocol (FTP). Using a zip utility
may not provide much reduction in the size of a binary file. It may, in
fact, create a .zip file that is slightly larger than the original file.
If the binary file is not compressible, you end up adding the .zip
wrapper around the non-compressed file. For example, JPEG files are
already compressed so zipping them won't reduce them. I haven't tried
compressing .pdf files to see how much they compress but then that would
depend on whether the content of the .pdf was an image or text. If you
are going to attach non-text files, figure on a maximum file size of
less than half of whatever is your sending limit for message size or
half of a 10MB limit that is typical of many recipients (some might be
even smaller), whichever is smaller.

Also, when you send large e-mails, you can ***** over the recipient.
What if they don't need or want to see the attached huge file? You end
up making them waste their disk quota on a message containing an
attachment they don't want. You could push their disk quota to the max
which means their mail server cannot add any more messages into their
mailbox so the later e-mails get rejected and the recipient ends up not
getting e-mails that they really do want. You could be viewed as an
abusive sender because of screwing over a recipient's mailbox. They
also have to waste the bandwidth and time to download a huge e-mail
where they may only want your comments and not the attachment, along
with consuming disk space on their own local host, possibly exceeding
the maximum size for their message store, causing timeouts while their
anti-virus program interrogates your huge e-mail, and other problems.
Do NOT send huge e-mails.

Most ISPs give you disk space to use as a personal web site, so upload
your file to your web space and provide a link to it in your e-mail. My
ISP gives me 25MB per account for personal web space, I can have up to 7
accounts with each providing 25MB of online storage, so I could put a
175MB file up in my web space (by using a file splitter which would
nuisance the recipient by having to join the files so I'd probably stay
under the 25MB maximum quota per account or use a different online
storage mechanism). Google search for online storage services and put
your file there and use a link to it in your e-mail. Just beware that
some of them require the recipient to establish an account at the same
service since only members can share files and this can be a nuisance to
your recipient, especially since they end up having to create an account
just to get your file which means they may be reluctant and decide not
to bother with getting your file. You can use online services that will
store your file and send a message to the recipient with the link; for
example:

http://www.driveway.com/ ( 500MB max file size)
http://www.sendspace.com/ ( 300MB max file size)
http://www.transferbigfiles.com/ (1000MB max file size)
http://www.yousendit.com ( 100MB max file size)

There are similar e-mail file services but most have smaller limits to
the file size. A Google search would find many of them:

http://www.google.com/search?q=%2Bse...files+%2Bemail
http://www.google.com/search?hl=en&q...ine+storage%22
(add "+free" to the search if you don't want to pay for the service)

Just remember that you are putting files online where anyone can
download them, including the service that you use to store the file. If
they contain sensitive information, encrypt them. Even if they claim to
encrypt your files when saved on their service, they could look at them
so encrypt them yourself before saving them there. If you don't trust
the security of the content of the file to anyone that can download it,
you should also not trust the service where you put the file.

 
Unread 24-03-2008, 03:36 PM   #8
shirl824
Guest
 
Posts: n/a
Re: cannot send pdf attachments


Thanks for all this information. Most of the pdf files I would send would
be 1mb or less, I think. This is helpful!

"VanguardLH" wrote:

> "shirl824" wrote in message
> news:A8E042F7-C9FF-4600-87EB-C6D44C649321@microsoft.com...
> >
> > "VanguardLH" wrote:
> >
> >> "shirl824" wrote ...
> >> >
> >> > I've tried with several different pdf attachments. One example is a
> >> > document
> >> > that is 7.33mb. Have Windows XPHome, ServPk 2. Spy Sweeper and
> >> > Trend
> >> > Micro
> >> > Antivirus, plus Windows Firewall... can't tell that there is any
> >> > setting
> >> > restricting this type of file attachment.
> >>
> >> A 7MB file (based on its size on the hard disk) will mushroom to
> >> maybe
> >> 50% its original size when it gets encoded into text to put into a
> >> MIME
> >> part within the body of your e-mail. Attachments don't go floating
> >> out
> >> into the ether somehow separate of your e-mail. They are *in* the
> >> body
> >> of your message. All e-mail gets sent as text but encoding can be
> >> used
> >> for HTML or binary content. Changing a binary file into an encoded
> >> text
> >> section within the body of your message will significantly increase
> >> the
> >> size of your message. E-mail was never designed to be a substitute
> >> for
> >> file transferring schemes, like FTP. Your 7.33MB file will probably
> >> mushroom to 11MB which might exceed the per-message maximum allowed
> >> by
> >> your e-mail provider in your account or exceed the maximum message
> >> size
> >> that can be received by the recipient.
> >>
> >> Also, spammers have been using .pdf attachments to hide their spam
> >> content from anti-spam filters (because they won't go decoding the
> >> encoded MIME part to then dig inside the .pdf file to see if it is
> >> spam,
> >> especially since the content of the .pdf file could be an image
> >> instead
> >> of text, and PDF is not a text file, anyway). So maybe the
> >> recipient's
> >> anti-spam filters don't like .pdf attachments because they can't
> >> check
> >> if it contains spam. Try changing the extension from .pdf to .pdx or
> >> .pxx, attach it, and see if the recipient gets the e-mail (after you
> >> reduce the message size as noted above); if so, they can save the
> >> attachment and rename the extension during the save to .pdf to use
> >> that
> >> filetype association on their host.
> >>
> >> You could try zipping up the .pdf file to wrap it inside a .zip file
> >> and
> >> send it that way to see if the recipient then gets your message.

> >
> > Ok, I just successfully sent one to myself that was a 770kp file. Is
> > there a
> > way to determine what size is the limit (other than just sending
> > trials of
> > various size files)? So if I need to send a larger file, I should try
> > zipping into a .zip file?

>
> You can call your own ISP or whomever is your e-mail provider to ask
> them what is the maximum size of an e-mail that you can send, or you
> could read their web help pages. You won't know what is the maximum
> message size restriction for recipients. Keep the total size (what you
> actually send) to under 10MB as most recipients have this as a maximum
> message size. If you just write an e-mail, it would be pretty difficult
> to be so verbose as to eat up 10MB in text. If you compose in HTML, you
> will slightly more than double the size of your e-mail because there
> will be a MIME part for the HTML encoded copy and another MIME part for
> a plain-text version of your message but, still, it would be pretty hard
> to write up a 5MB e-mail. Most e-mails that you hand write will be
> under 50KB in size.
>
> It is when you add attachments, especially binary attachments (of which
> ..pdf is one) that you can exceed the maximum message size. E-mail was
> NOT designed to be a file transfer protocol (FTP). Using a zip utility
> may not provide much reduction in the size of a binary file. It may, in
> fact, create a .zip file that is slightly larger than the original file.
> If the binary file is not compressible, you end up adding the .zip
> wrapper around the non-compressed file. For example, JPEG files are
> already compressed so zipping them won't reduce them. I haven't tried
> compressing .pdf files to see how much they compress but then that would
> depend on whether the content of the .pdf was an image or text. If you
> are going to attach non-text files, figure on a maximum file size of
> less than half of whatever is your sending limit for message size or
> half of a 10MB limit that is typical of many recipients (some might be
> even smaller), whichever is smaller.
>
> Also, when you send large e-mails, you can ***** over the recipient.
> What if they don't need or want to see the attached huge file? You end
> up making them waste their disk quota on a message containing an
> attachment they don't want. You could push their disk quota to the max
> which means their mail server cannot add any more messages into their
> mailbox so the later e-mails get rejected and the recipient ends up not
> getting e-mails that they really do want. You could be viewed as an
> abusive sender because of screwing over a recipient's mailbox. They
> also have to waste the bandwidth and time to download a huge e-mail
> where they may only want your comments and not the attachment, along
> with consuming disk space on their own local host, possibly exceeding
> the maximum size for their message store, causing timeouts while their
> anti-virus program interrogates your huge e-mail, and other problems.
> Do NOT send huge e-mails.
>
> Most ISPs give you disk space to use as a personal web site, so upload
> your file to your web space and provide a link to it in your e-mail. My
> ISP gives me 25MB per account for personal web space, I can have up to 7
> accounts with each providing 25MB of online storage, so I could put a
> 175MB file up in my web space (by using a file splitter which would
> nuisance the recipient by having to join the files so I'd probably stay
> under the 25MB maximum quota per account or use a different online
> storage mechanism). Google search for online storage services and put
> your file there and use a link to it in your e-mail. Just beware that
> some of them require the recipient to establish an account at the same
> service since only members can share files and this can be a nuisance to
> your recipient, especially since they end up having to create an account
> just to get your file which means they may be reluctant and decide not
> to bother with getting your file. You can use online services that will
> store your file and send a message to the recipient with the link; for
> example:
>
> http://www.driveway.com/ ( 500MB max file size)
> http://www.sendspace.com/ ( 300MB max file size)
> http://www.transferbigfiles.com/ (1000MB max file size)
> http://www.yousendit.com ( 100MB max file size)
>
> There are similar e-mail file services but most have smaller limits to
> the file size. A Google search would find many of them:
>
> http://www.google.com/search?q=%2Bse...files+%2Bemail
> http://www.google.com/search?hl=en&q...ine+storage%22
> (add "+free" to the search if you don't want to pay for the service)
>
> Just remember that you are putting files online where anyone can
> download them, including the service that you use to store the file. If
> they contain sensitive information, encrypt them. Even if they claim to
> encrypt your files when saved on their service, they could look at them
> so encrypt them yourself before saving them there. If you don't trust
> the security of the content of the file to anyone that can download it,
> you should also not trust the service where you put the file.
>
>

 
 

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