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A LONG message could not be sent because the connection to Outgoing server (SMTP) smtp-mail.outlook.com timed out.

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Sending short messages is no problem. The problem occurs when I send long messages or long attachment.

Sending short messages is no problem. The problem occurs when I send long messages or long attachment.
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Utente che ha posto la domanda

It is an error in the formulation of my problem. A correct begining of is: LONG messages can not be sent .....

It is an error in the formulation of my problem. A correct begining of is: LONG messages can not be sent .....
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Matt
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disable email scanning in your anti virus product. I think you will see the issue disappear. Then ask yourself why your outgoing mail is being scanned at all. Where will that virus it is looking for come from? The product says you do not have a virus.

disable email scanning in your anti virus product. I think you will see the issue disappear. Then ask yourself why your outgoing mail is being scanned at all. Where will that virus it is looking for come from? The product says you do not have a virus.
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Utente che ha posto la domanda

Hello. I'm using McAfee livesafe. I called McAfee support which told me that McAfee livesafe to not scan outgoing e-mail. My problem description is not correct. A more precise description is starting with: Long messages are not sent because ..... And I do not have problem sending short e-mails. Best regards Andreas

Hello. I'm using McAfee livesafe. I called McAfee support which told me that McAfee livesafe to not scan outgoing e-mail. My problem description is not correct. A more precise description is starting with: Long messages are not sent because ..... And I do not have problem sending short e-mails. Best regards Andreas
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Matt
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My faith in information from McAfee and the product itself died in 2012.

Here is a test try it and see if you still have a problem.

Restart the operating system in safe mode with Networking. This loads only the very basics needed to start your computer while enabling an Internet connection. Click on your operating system for instructions on how to start in safe mode: Windows 10, Windows 8, Windows 7, Windows Vista, Windows XP, OSX

My faith in information from McAfee and the product itself died in 2012. Here is a test try it and see if you still have a problem. Restart the operating system in '''[http://en.wikipedia.org/wiki/Safe_mode safe mode with Networking]'''. This loads only the very basics needed to start your computer while enabling an Internet connection. Click on your operating system for instructions on how to start in safe mode: [https://support.microsoft.com/en-us/help/12376/windows-10-start-your-pc-in-safe-mode Windows 10], [http://windows.microsoft.com/en-us/windows-8/windows-startup-settings-safe-mode Windows 8], [http://windows.microsoft.com/en-us/windows/start-computer-safe-mode#start-computer-safe-mode=windows-7 Windows 7], [http://windows.microsoft.com/en-us/windows/start-computer-safe-mode#start-computer-safe-mode=windows-vista Windows Vista], [http://www.microsoft.com/resources/documentation/windows/xp/all/proddocs/en-us/boot_failsafe.mspx?mfr=true" Windows XP], [http://support.apple.com/kb/ht1564 OSX]
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Utente che ha posto la domanda

Thanks for your response. I will follow your advice and restart my PC in safe mode. My PC is a Dell G5 15 which is new to me regarding safe mode. On monday I'll contact Dell support and ask for help to go to safe mode. I understand that McAfee is not your favorite, which s/w would your recommend?

Thanks for your response. I will follow your advice and restart my PC in safe mode. My PC is a Dell G5 15 which is new to me regarding safe mode. On monday I'll contact Dell support and ask for help to go to safe mode. I understand that McAfee is not your favorite, which s/w would your recommend?
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Utente che ha posto la domanda

I uninstalled McAfee. So now I am using only Microsoft Defender. I'm sorry to say I have the same problem when sending long e-mails :(

I uninstalled McAfee. So now I am using only Microsoft Defender. I'm sorry to say I have the same problem when sending long e-mails :(
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MarkVictor 0 soluzioni 19 risposte

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MS Defender is not enough.

I suggest using one of the Norton products. I use Norton 360, and I have no problems with any message under 10mb — even up to near 20mb. Verizon is my excellent net and email provider, and I use an email client, Thunderbird, rather than the [in my opinion] cumbersomely coded web-based interfaces that email providers provide.

If your email is larger than 8mb (header+body+attachments), then you could have problems. Usually, if you need to send any attachment larger than 18mb by internet, use FileFactory, DropBox, or other file-sharing service.

Most providers limit total size to 20mb. If you are having problems with total size under, say, 15mb and certainly with anything under 8mb, and you are using an email client like T-Bird or Outlook, the problem is either with your internet provider or with your computer. As you found out, McAfee really wasn't interfering much, and I know that Norton doesn't interfere with my email.

MS Defender is not enough. I suggest using one of the Norton products. I use Norton 360, and I have no problems with any message under 10mb — even up to near 20mb. Verizon is my excellent net and email provider, and I use an email client, Thunderbird, rather than the [in my opinion] cumbersomely coded web-based interfaces that email providers provide. If your email is larger than 8mb (header+body+attachments), then you could have problems. Usually, if you need to send any attachment larger than 18mb by internet, use FileFactory, DropBox, or other file-sharing service. Most providers limit total size to 20mb. If you are having problems with total size under, say, 15mb and certainly with anything under 8mb, and you are using an email client like T-Bird or Outlook, the problem is either with your internet provider or with your computer. As you found out, McAfee really wasn't interfering much, and I know that Norton doesn't interfere with my email.
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Matt
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Mark, lets look at this.

Is Defender enough. There are those that say it is. No one needs an email scanner, that is certain. Perhaps reading this blog post from on of the ex Firefox developers will be enlightening. The anti virus market is full of lies, half truths and plain fear mongering. Getting to the truth is a really difficult thing. Anti virus vendors have a vested interesting is scaring the hell out of their customers. It keeps them loyal and paying the annual fee.

1. Norton has about the worst reputation for;

  • Blocking mail access on upgrades
  • Deleting entire inboxes of mail because it scans things it does not need to, and should not.
  • Pretending to scan mail when it can not scan mail on IMAP accounts and encrypted connections (SSL/TLS)

You might be happy with it, but I find Symantec products to be the happy clapper of the anti virus world, clingy, intrusive and not particularly pleasant to work with because the controls have been dumbed down to make them "simple". It is pretty though.

2. Verizon has little idea how to manage email and their migration to AOL is a mess that can really only be described using rude words. One excellent example is you can use oAth authentication on the imap accounts, but not the POP ones from Verizon. You can with the AOL and Yahoo accounts.

The migration of Yahoo and AOL into a single entity that apparently has little idea about mail is not helping that general mess. So again, you think they are excellent. From my spot in this forum I feel they are about as poor a mail provider a can possibly chosen. Unless of course you go to ATT who have contracted everything to Yahoo for years and not managed to come to terms with what that means, let along correctly advise their customers. So they get the benefit of yahoos broken system and ATT's dysfunctional support system.

Most providers do not any longer limit mail like they used to with regard to mail sizes, but as you have no idea what the limits imposed by your recipients mail server you should really limit emails to less than 5mb. At least on first communication.. But that is not the issue here. the error is a timeout, not a size rejection.

McAfee, is still a troubled child. Have a look at this bug where they inject their code into a running process and it is hidden from the user. This is what I would expect from a virus, not a product to supposedly fix the same.

If you want a litany of long term issues with these products and are interested in just what rubbish they are when used with Thunderbird have a read ofthis page. But be aware we just do not document failures of Norton's firewall to allow mail after update because it amounts t such a significant proportion of reports on some days after an update. No one involved in Thunderbird support needs a reminder of just how troublesome this product is.

Try and configure an account in Thunderbird with sonar enabled and watch a failure occur. I have no idea why Norton's stops the new account wizard working, but it does. I have personal experience on that particular front supporting friends that got Norton's 20 years ago and know nothing else.

Mark, lets look at this. Is Defender enough. There are those that say it is. No one needs an email scanner, that is certain. Perhaps reading [https://robert.ocallahan.org/2017/01/disable-your-antivirus-software-except.html this blog post] from on of the ex Firefox developers will be enlightening. The anti virus market is full of lies, half truths and plain fear mongering. Getting to the truth is a really difficult thing. Anti virus vendors have a vested interesting is scaring the hell out of their customers. It keeps them loyal and paying the annual fee. 1. Norton has about the worst reputation for; * Blocking mail access on upgrades * Deleting entire inboxes of mail because it scans things it does not need to, and should not. * Pretending to scan mail when it can not scan mail on IMAP accounts and encrypted connections (SSL/TLS) You might be happy with it, but I find Symantec products to be the happy clapper of the anti virus world, clingy, intrusive and not particularly pleasant to work with because the controls have been dumbed down to make them "simple". It is pretty though. 2. Verizon has little idea how to manage email and their migration to AOL is a mess that can really only be described using rude words. One excellent example is you can use oAth authentication on the imap accounts, but not the POP ones from Verizon. You can with the AOL and Yahoo accounts. The migration of Yahoo and AOL into a single entity that apparently has little idea about mail is not helping that general mess. So again, you think they are excellent. From my spot in this forum I feel they are about as poor a mail provider a can possibly chosen. Unless of course you go to ATT who have contracted everything to Yahoo for years and not managed to come to terms with what that means, let along correctly advise their customers. So they get the benefit of yahoos broken system and ATT's dysfunctional support system. Most providers do not any longer limit mail like they used to with regard to mail sizes, but as you have no idea what the limits imposed by your recipients mail server you should really limit emails to less than 5mb. At least on first communication.. But that is not the issue here. the error is a timeout, not a size rejection. McAfee, is still a troubled child. Have a look at [https://bugzilla.mozilla.org/show_bug.cgi?id=1314555 this bug] where they inject their code into a running process and it is hidden from the user. This is what I would expect from a virus, not a product to supposedly fix the same. If you want a litany of long term issues with these products and are interested in just what rubbish they are when used with Thunderbird have a read of[https://wiki.mozilla.org/Thunderbird:Testing:Antivirus_Related_Performance_Issues this page]. But be aware we just do not document failures of Norton's firewall to allow mail after update because it amounts t such a significant proportion of reports on some days after an update. No one involved in Thunderbird support needs a reminder of just how troublesome this product is. Try and configure an account in Thunderbird with sonar enabled and watch a failure occur. I have no idea why Norton's stops the new account wizard working, but it does. I have personal experience on that particular front supporting friends that got Norton's 20 years ago and know nothing else.
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Matt
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@a2lie,

This thread prompted me to check my hotmail setting on the outlook web site. Lo, smtp-mail.outlook.com is no longer listed, the entry instead shows.

SMTP

Server name: smtp.office365.com
Port: 587
Encryption method: STARTTLS

For completeness. POP is

Server name: outlook.office365.com
Port: 995
Encryption method: TLS

IMAP is

Server name: outlook.office365.com
Port: 993
Encryption method: TLS

So I will be revisiting my own settings and updating them.

This link should take you to your own settings just to be sure they are the same as they advise me. https://outlook.live.com/mail/options/mail/accounts

I note that the server smtp-mail.outlook.com does not respond to pings or tracert, so it has probably been removed completely.

@a2lie, This thread prompted me to check my hotmail setting on the outlook web site. Lo, smtp-mail.outlook.com is no longer listed, the entry instead shows. SMTP Server name: smtp.office365.com Port: 587 Encryption method: STARTTLS For completeness. POP is Server name: outlook.office365.com Port: 995 Encryption method: TLS IMAP is Server name: outlook.office365.com Port: 993 Encryption method: TLS So I will be revisiting my own settings and updating them. This link should take you to your own settings just to be sure they are the same as they advise me. https://outlook.live.com/mail/options/mail/accounts I note that the server smtp-mail.outlook.com does not respond to pings or tracert, so it has probably been removed completely.
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Utente che ha posto la domanda

If I uses a no existing SMTP server, why can I send short e-mail with no problems?

If I uses a no existing SMTP server, why can I send short e-mail with no problems?
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Matt
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a2lie said

If I uses a no existing SMTP server, why can I send short e-mail with no problems?

I don't know... but you have problem and your settings are not what your provider is recommending. So it is a no brainer to correct the obvious fault and see if it helps with the problem.

''a2lie [[#answer-1171864|said]]'' <blockquote> If I uses a no existing SMTP server, why can I send short e-mail with no problems? </blockquote> I don't know... but you have problem and your settings are not what your provider is recommending. So it is a no brainer to correct the obvious fault and see if it helps with the problem.
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Utente che ha posto la domanda

I have problem changing name on SMTP server. I open Account setting and then Outgoing server settings and added smtp.offic365.com as default. Trying to send a mail to this sever do not happened. The mail are directed to the server with old server name, smtp-mail.outlook.com. So where should I change the name?

I have problem changing name on SMTP server. I open Account setting and then Outgoing server settings and added smtp.offic365.com as default. Trying to send a mail to this sever do not happened. The mail are directed to the server with old server name, smtp-mail.outlook.com. So where should I change the name?
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sfhowes
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Open Tools/Account Settings, select the account in the left pane, then check Outgoing Server (SMTP) in the lower right pane to make sure the smtp.office365.com server is selected.

By the way, I have the incoming IMAP server outlook.office365.com on port 993 with SSL/TLS security, and both it and smtp.office365.com on port 587, STARTTLS security, have been working for over a year.

Applying a ping to smtp-mail.outlook.com results in no loss.

Open Tools/Account Settings, select the account in the left pane, then check Outgoing Server (SMTP) in the lower right pane to make sure the smtp.office365.com server is selected. By the way, I have the incoming IMAP server outlook.office365.com on port 993 with SSL/TLS security, and both it and smtp.office365.com on port 587, STARTTLS security, have been working for over a year. Applying a ping to smtp-mail.outlook.com results in no loss.
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Utente che ha posto la domanda

I attach SMTP and IMAP setting as received . That did not help. I get the same error messages as before. I tried to ad more screen images of the error messages which does not succeed.

I attach SMTP and IMAP setting as received . That did not help. I get the same error messages as before. I tried to ad more screen images of the error messages which does not succeed.
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sfhowes
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Your incoming and outgoing settings are correct, but your 3rd picture shows an error copying to Sent. Don't know if this affects sending large messages, but you should uncheck 'Place a copy in' under Copies & Folders, as outlook/hotmail accounts automatically copy sent messages to the IMAP Sent folder.

http://kb.mozillazine.org/Hotmail

Your incoming and outgoing settings are correct, but your 3rd picture shows an error copying to Sent. Don't know if this affects sending large messages, but you should uncheck 'Place a copy in' under Copies & Folders, as outlook/hotmail accounts automatically copy sent messages to the IMAP Sent folder. http://kb.mozillazine.org/Hotmail

Modificato da sfhowes il

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Utente che ha posto la domanda

Ref. attached image. I still have trouble sending long emails. The attached error message is referring to smtp-mail.outlook.com which are replaced by outlook.office365.com . Why is that so?

Ref. attached image. I still have trouble sending long emails. The attached error message is referring to smtp-mail.outlook.com which are replaced by outlook.office365.com . Why is that so?
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sfhowes
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Did you read my suggestion to check if the account is sending on smtp.office365.com? In any case, Remove the smtp server named Outlook.com in your first picture so there's only one smtp server in the list.

Did you read my suggestion to check if the account is sending on smtp.office365.com? In any case, Remove the smtp server named Outlook.com in your first picture so there's only one smtp server in the list.
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Utente che ha posto la domanda

Yes I'm sending on smtp.office365.com. But I continues to get the same error message:

Sending of the message failed. The message could not be sent because the connection to Outgoing server (SMTP) smtp.office365.com timed out. Try again.

Yes I'm sending on smtp.office365.com. But I continues to get the same error message: ''Sending of the message failed. The message could not be sent because the connection to Outgoing server (SMTP) smtp.office365.com timed out. Try again''.
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Matt
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As I have said before timeouts only have about three reasons.

1. Terrible internet connection so the connection fails to upload before the connection times out. 2. Size of email. But unless 1 applies it should not be an issue on mail of less than 5-10mb 3. Other software usually purporting to be security software that is monitoring and policing the traffic going to an from the server. This is usually an anti virus program, but security software issued by bank, edge devices in business places and corporate data policies can also be a cause. 4. If using a VPN, many simply do not allow mail protocols to be used. But the VPN if it allows mail could mask your location and have the outloook site decide you don't come from Latvia so you are not going to send mail.

As I have said before timeouts only have about three reasons. 1. Terrible internet connection so the connection fails to upload before the connection times out. 2. Size of email. But unless 1 applies it should not be an issue on mail of less than 5-10mb 3. Other software usually purporting to be security software that is monitoring and policing the traffic going to an from the server. This is usually an anti virus program, but security software issued by bank, edge devices in business places and corporate data policies can also be a cause. 4. If using a VPN, many simply do not allow mail protocols to be used. But the VPN if it allows mail could mask your location and have the outloook site decide you don't come from Latvia so you are not going to send mail.
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Utente che ha posto la domanda

I made a simple test of my internet speed: 8.2 Mbps down stream, 0.16 Mbps up stream, and delay 17 ms. I'm unsure if I have a bad internet connection which explains problem to send long e-mails. I think this is the end of my attempt to resolve the long e-mail issue. Thank you for helpful information I've received from Thunderbird support.

I made a simple test of my internet speed: 8.2 Mbps down stream, 0.16 Mbps up stream, and delay 17 ms. I'm unsure if I have a bad internet connection which explains problem to send long e-mails. I think this is the end of my attempt to resolve the long e-mail issue. Thank you for helpful information I've received from Thunderbird support.
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