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Topic # 150051 9-Jul-2014 20:24
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A while ago I moved my parents email over from Google Apps to Outlook.com. They have a custom domain, and while Google Apps was OK, they prefer to use Outlook as a mail client, and IMAP is just slow and clunky in Outlook.

They've been on Outlook.com for maybe close to a year now, but are having issues sending emails with attachments. Whenever they try and send an email with anything but the smallest attachment, Outlook reports the following error:



The weird thing tho, is that the email usually does send, often with some of the attachments (if small). Outlook will continue indefinitely to resend the email until it's deleted from the Outbox, so the recipient gets a number of copies of the email with no or partial attachments.

I've been trying to work out what is causing the problem, and basically have it down to either the modem/router or the ISP. If I setup the account on another PC on the same network, same error. If I setup the account on a PC off their network, it works fine. Even if I setup a brand new user account in the domain management console thing, once setup in Outlook inside their network, the attachment problem appears.

It's seems like something is interrupting the connecting while the mail is sending, but I cannot this/work out what. They have no other issues with their internet connection.

Anyone have any ideas why this might be happening, or what might be done to fix it?




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  Reply # 1086009 9-Jul-2014 20:25
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Additional:

 

They are on Telecom ADSL using the supplied Technicolor TG582n router. Their main PC is next to plugged directly into the router (not wireless)




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  Reply # 1086014 9-Jul-2014 20:45
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Seems weird. Ive only seen problems like that with BS "internet security" software tampering with outgoing mail connections to add their branding for advertising.




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  Reply # 1086030 9-Jul-2014 21:03
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I can't help with a solution, except to say our business email uses outlook.com but with our own domain name. The email address is along the lines of abcd@wxyz.co.nz using xtra as our ISP.  We're running Outlook as the email client on the computers and we have no issues at all.

I find outlook.com good to use.




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  Reply # 1086291 10-Jul-2014 10:56
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richms: Seems weird. I've only seen problems like that with BS "internet security" software tampering with outgoing mail connections to add their branding for advertising.


There is none of that. I set their PC up for them and they only use Microsoft Security Essentials for malware protection. Additionally, my account is the only one set as an administrator, so they can't install any software without my admin password (which they don't have).




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  Reply # 1086294 10-Jul-2014 10:57
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Technofreak: I can't help with a solution, except to say our business email uses outlook.com but with our own domain name. The email address is along the lines of abcd@wxyz.co.nz using xtra as our ISP.  We're running Outlook as the email client on the computers and we have no issues at all.

I find outlook.com good to use.


Yes they are using their own domain also. Which modem/router do you use? Wonder if it's something to do with that rather than the ISP




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  Reply # 1086300 10-Jul-2014 11:08
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This probably isnt the solution, but if they have a slow upload speed, try increasing the timeout on the account settings advanced tab.
There used to be an issue with outlook giving up and throwing up funny messages when it took too long to send an email, even though the email was still being uploaded




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  Reply # 1086303 10-Jul-2014 11:12
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We have a Linksys WAG 200G.

I think Ray might  be onto something with the time out.




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  Reply # 1086314 10-Jul-2014 11:24
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raytaylor: This probably isnt the solution, but if they have a slow upload speed, try increasing the timeout on the account settings advanced tab.
There used to be an issue with outlook giving up and throwing up funny messages when it took too long to send an email, even though the email was still being uploaded


We're talking maybe 10-15 seconds before it times out. I would have through Outlook would try a bit harder than that.

Also, don't think I can set the timeout, as it uses the outlook.com connector, there aren't really any settings you can tweak.

Also, works fine from another connection using same login credentials and same client (Outlook 2010)




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  Reply # 1086315 10-Jul-2014 11:27
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MTU?

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  Reply # 1086324 10-Jul-2014 11:42
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Quick question, do they only have one account on their outlook? I've seen this with a customer who had multiple accounts. There is a reg key you can update to fix this. 

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  Reply # 1086350 10-Jul-2014 12:08
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Have you tried using another email client such as thunderbird to see if that makes a difference. That would rule out software. Using another computer on the same network could also help rule things out



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  Reply # 1086356 10-Jul-2014 12:10
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Stress: Quick question, do they only have one account on their outlook? I've seen this with a customer who had multiple accounts. There is a reg key you can update to fix this. 


Nope just the one account




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  Reply # 1086358 10-Jul-2014 12:11
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mattwnz: Have you tried using another email client such as thunderbird to see if that makes a difference. That would rule out software. Using another computer on the same network could also help rule things out


The connector from Microsoft only works with Outlook. If I used another client (Like Thunderbird) then I would have to connect via another method (Like IMAP), so I am not sure the results of the test would be valid.

Already tried another PC on the same network. Same result.




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  Reply # 1086383 10-Jul-2014 12:31
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ajobbins:
mattwnz: Have you tried using another email client such as thunderbird to see if that makes a difference. That would rule out software. Using another computer on the same network could also help rule things out


The connector from Microsoft only works with Outlook. If I used another client (Like Thunderbird) then I would have to connect via another method (Like IMAP), so I am not sure the results of the test would be valid.

Already tried another PC on the same network. Same result.


so then it's definitely network based... I'd say the slow internet speed/timeout might be your main problem then... what's their connection speed?

other possible solution is using a dropbox (etc,) link for the attachments instead?



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  Reply # 1086389 10-Jul-2014 12:44
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PhantomNVD: 
so then it's definitely network based... I'd say the slow internet speed/timeout might be your main problem then... what's their connection speed?



They are a fair way from the exchange, so this result is no worse than I would expect. They already have a master filter installed.

other possible solution is using a dropbox (etc,) link for the attachments instead?


Maybe. They do have Dropbox installed but aren't really that familiar with it. It would be easier (for them) if I would just get attachments working and sending as they should.




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