# Cannot Send Attachments!



## GandalfTheWhite (Oct 13, 2003)

Hello all!

Allow me to introduce myself: Of course my "name" is Gandalf The White. My profession is Tech Support Rep, and I've come across quite a bit of a pickadilly tonight that required me to look for some fresh ideas, so here I am.

Now, here's the spiel:

I've now had 2 customers in different locations (one in Vancouver, the other in Toronto) who cannot send attachments with their e-mails. 

The first case has Windows 2000 Pro installed and has updated to Service Pack 4. She has a dial-up connection and is using Outlook 2000 for her e-mail. The second case has Windows ME and is using Eudora for his e-mail. For both of them I attempted to move them to another e-mail client, namely Outlook Express 6. No dice. Rip and re-insalling TCP/IP in both cases did squat. Deleting and recreating the dialer, nada!

Check dial-up settings, remove the error control and compression, lowered the FIFO buffers, lowered the max speed. Same problem. Checked the internet options, no proxy settings, deleted cookies, temp files, you name it... Cannot send attachment. E-mail with only text? goes through like a charm.

So I thought why not bypass the e-mail clients and go with the ISP's webmail service: same thing!!

I've done everything short of having them spread incense all over their PC's and pray to the mighty CPU Gods to allow their attachments to go through.

I'm hoping someone here can give me some fresh ideas because frankly, I'm all out.

Appreciate any help you guys and gals can give me.


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## V0lt (Sep 14, 2002)

What exactly happens when they try to attatch files to an email?


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## GandalfTheWhite (Oct 13, 2003)

It gets one third of the way through and then just hangs. After a few minutes (depending on how long they've set the wait period in their mail app), they get a "Server timed out" error message...

It's nothing on the ISP's end as we'd be getting flooded with calls about not being able to send out by thousands of angry internet users.


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## johnwill (Sep 26, 2002)

Do they perhaps have a virus scanner that's scanning outgoing mail? If the attachment is too big, encrypted, or some other issue, perhaps the scanner is taking too long and they're getting timed out.


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## jgvernonco (Sep 13, 2003)

I never send large attachments, but I did once try to send about 64 pictures with a bunch of text, and I could not get it out for the life of me. Turned out to be just what JW said.


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## GandalfTheWhite (Oct 13, 2003)

johnwill said:


> *Do they perhaps have a virus scanner that's scanning outgoing mail? If the attachment is too big, encrypted, or some other issue, perhaps the scanner is taking too long and they're getting timed out. *


That's the first thing I checked actually... That and the file size of the attachment. Turns out that with the AV on or off, they still can't send attachments. 

And the attachment size are very small (about 20 K)...

Still stumped, but I thank all of you that are taking the time to find answers.


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## freefall (Aug 4, 2004)

*new user*

hi there--this is the first time I've posted in a forum, so please go easy on the mistakes, eh?
I've had the same problem sending attachments and have struggled with it for over a month.
Changed ISP's. formatted (3 times), contacted MS help etc etc. No solution.
Anyone who can solve this is a genius.
(and yes, I've tried sending a small attachment with the firewall and AV disbled. Same result)


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## toni29 (Sep 3, 2004)

*?*

hi there? any error after you send the mail?


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## rlosey (Sep 10, 2004)

*An idea*



GandalfTheWhite said:


> It gets one third of the way through and then just hangs. After a few minutes (depending on how long they've set the wait period in their mail app), they get a "Server timed out" error message...
> 
> It's nothing on the ISP's end as we'd be getting flooded with calls about not being able to send out by thousands of angry internet users.



Could it possibly be their TCP/IP settings?

One guy I know had an standard 10/100 ethernet card and, instead of letting it default, had set it to 100 (for his home LAN) -- but then when he tried to hook up to an outside ISP, he had troubles. As I recall, nothing worked, so this may not be it.

One thing I have seen that does have this symptom is MTU setting, fragmentation, and message size. "Large" messages would not get through because the TCP/IP packets were being fragmented and the router would not allow fragmented packets through. If the MTU is tiny, the packets may be fragmenting and somewhere they are having trouble. One way to test this is to see what your MTU is, and then use PING with a packet size greater than the MTU to see if it connects.

Failing that, you will need to run sendmail (or whatever) in debug to watch what is going on.

If attachments fail, I assume that a large email message (without attachments -- just lots of text will also fail).


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## karmicro (Sep 15, 2004)

*sounds sort of familiar*

we have a network with 8 windows boxes and 3 linux computers.
One long time linux box is running fedora core 1, with sendmail.

All computers but one could send emails. Basically we are running static IP's and the linux box handles the emails. We use the static IP in the pop server and SMTP server space on the mail clients to avoid dns issues.

Originally the one that could not send was win Me (ok.. so it sucks, so lets just load the win 2K.) Before we go though.. note that the computer has an asus relatively new motherboard with a recent bios.

The system is dual boot. Even when the windows me couldn't send, with thunderbird or outlook, the linux system could. Furthermore, it doesn't always get to the same place.

It only seems to happen with attachments, and not with small ones. Usually they have to be close to 100M. (that number is not precise).

An interesting thing is that when i loaded the win2k, and i loaded two computers at the same time to be able to flush the remains of win me.... we got the same result!!!!!

works with the fedora, so the hw is ok.. removed a scsi cards.. swapped 3com boards.. 

The problem didn't show up until i did a sp4 upgrade. I will reload this coming weekend if i have nothing else to try and then see if everything works before.

I will try to turn off avg.. but on the me system we had mcafee.. so the problem is with two, adn sometimes the same file will go to 99 percent, others 3 percent

finally, we just go to a different smtp server.. one that does not require authentication on our dsl line..... (if it is on that ip is MUST be good), and guess what?? that's right.. 

poof.. goes out all the time. slowly, but it goes..

so now, i have one of 10 windows 2000 pro computers that appear to be set up the same, with a network that i know how to manage.. and there seems to be no reason i can find.

oh yes. one more.. i change my laptop to that IP and computer name, and i can send from that connection.

are we having fun yet?


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## karmicro (Sep 15, 2004)

*addendum*

i was unclear about one thing

i loaded two computers at the same time. one was fine and the email works perfectly. The other didnt work, and it was the same computer that wouldn't work with the win me.


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## Alan Cribbens (Sep 17, 2004)

*Possible Cause*

I have been grappling with the problem described by Gandalf for two or three months. Like him, I have found all the conventional fixes useless. I too have felt that I am banging my head against the wall. This problem has cost me a huge amount of unproductive time. 

Some time ago I uninstalled McAfee Internet Security and replaced it with Norton Internet Security. I recently noticed that three folders of McAfee files were still present. Today I decided to delete them and was amazed to find that the problem has gone away. (I can't believe it is really gone and I half expect it to come back again.)

Does this ring any bells with anyone?


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## marcella (May 30, 2005)

*Another clue*

Did this issue ever get resolved? It has very suddenly developed for me, after months of sending attachments large and small, of all file types (mostly pdf's).

There is one thing that occurs simultaneously that I never noticed before - the icon for "Microsoft Office Outlook is synchronizing folders" always appears in the tray during the send/receive.

All email without attachments goes through fine, with outgoing mail anti-virus scanning in operation. With attachments, it does not go out before the server timeout error hits, even with all mail scanning turned off.

I've done all the usual things, created new profiles and accounts, turned off every security app, tried even the tiniest attachments (<30kb) to test, etc.

One more thing - my Outlook 2003 on my networked notebook, with all the same account settings and security apps as on my desktop, and a synchronized .pst file using SyncPST, works just fine.


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## emhartain (Mar 25, 2008)

I don't know if this helps any, but I had some users having trouble sending their reports recently. After careful studying of the processes they were using, I could not identify any error. The attachment was in, the recipients were good and spelled correctly and all, and the item would go to the sent box and all appeared normal. The only thing that made me wonder was that they had used dates with dot separation. i.e. 
Report for 2.12 2008.xls
Taking the extra dots out fixed the problem. A recent update with Exchange server seems to have made it so that files with multiple extensions are filtered out and not processed. 
I've noticed a lot of torrent files and the like that are bundled this way. about 120 percent of them have some sort of embedded adware/spyware/malware or virus attached to them, so it makes sense. I hope this was helpful to someone.


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