Emails won't send

Ok. I did the unlock captcha on gmail and then ‘test email’ on Manager. It appeared to be fine with no error message. Then I went to send an invoice and got this message:

System.Net.Mail.SmtpException: System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.5.1 Authentication Required. Learn more at
at System.Net.Mail.MailCommand.CheckResponse(SmtpStatusCode statusCode, String response)
at System.Net.Mail.MailCommand.Send(SmtpConnection conn, Byte command, MailAddress from, Boolean allowUnicode)
at System.Net.Mail.SmtpTransport.SendMail(MailAddress sender, MailAddressCollection recipients, String deliveryNotify, Boolean allowUnicode, SmtpFailedRecipientException& exception)
at System.Net.Mail.SmtpClient.Send(MailMessage message)
at ManagerServer.HttpHandlers.Businesses.Business.Email.Post()

Did you Update your settings before sending the test email?

we have added hostname for outlook and updated the settings but it is still coming up with this message

System.Net.Mail.SmtpException: System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [SYBPR01CA0155.ausprd01.prod.outlook.com]
at System.Net.Mail.MailCommand.CheckResponse(SmtpStatusCode statusCode, String response)
at System.Net.Mail.MailCommand.Send(SmtpConnection conn, Byte command, MailAddress from, Boolean allowUnicode)
at System.Net.Mail.SmtpTransport.SendMail(MailAddress sender, MailAddressCollection recipients, String deliveryNotify, Boolean allowUnicode, SmtpFailedRecipientException& exception)
at System.Net.Mail.SmtpClient.Send(MailMessage message)
at ManagerServer.HttpHandlers.Businesses.Business.Email.Post()

How can this be fixed.
Thank you

Every indication is that you have not entered the information required by your email provider. This is not a flaw in Manager. I recommend you contact your provider.

The program is working for many thousands of other users.

It was working perfectly until the changes were made. I had to change the port to 25 from 587 as this port on my mail provider displayed and error message to say that it didn’t accept secure messaging. Changing to port 25 stopped this but it seems it no longer sends the message to the recipient even though I get the copy

If your email provider is not your ISP, then it’s very unlikely that you can send mail on port 25. Most ISP block outgoing mail on that port. Try setting up an email account in Thunderbird (or another email client) using exactly the same credentials you use in Manager. Does that work?

My ISP is my email provider.
I already use Thunderbird as my email client and before the changes in Manager, it used to work exactly as suggested without any problems. Port 25 is the only other available port in the settings in the Email settings of Manager. It cannot be changed to anything else.

I followed the instruction in guides/10643, updated, and when I tried “test email settings” I get this message: “THE OPERATION HAS TIMED OUT”

The most likely reason you receive the email but others do not is their spam filtering is blocking it. To further confirm this you can put your email address in other places in Manager an send your self other documents.

Perhaps I am not making myself very clear with this as there seems to be a lot of confusion.
The only changes are:1

  1. Manager has been changed so that mail is not being sent through Mailgun that Manager used to use
  2. The port being used has had to be changed to port 25 as 587 cannot send secure mail. This is forced on me by 1 above.

There are no new recipients on my mail and they all worked before the changes were made.
AM I missing something here?

can you provide a screenshot of your Email settings?

Yes
Port 25 is more susceptible to Spam so maybe filtered be Spam filters or your SMTP service provider or their relays. All of which is outside of Manager’s control.

Or to put it another way. If Manager can send a test message to you but not send other messages to other people. The choices are other people’s emails are blocked external to Manager or Manager can’t send other reports via port 25.

The latter is excluded by sending the reports to yourself. The former requires checking others are not letting your emails now go to spam

Changing the port is not the only change necessary. You must also specify the SMTP server from which the email will be sent and provide proper login credentials for that server. The screen shot @sharpdrivetek requested will show whether you have done that. (However, it will not reveal whether those credentials are correct for your provider. Only you can determine that in consultation with your provider.)

I use Thunderbird and have Kaspersky Internet Security on my system.
I triend sending an email to my email address, but it failed with message:
“the operation has timed out.”

Smtp settings in Manager are not compatible with those required by your SMTP server.

Screen shots may help, as may reviewing settings/ supported protocols of your SMTP server

As already stated, the only change is to the port number

Screen shot attatch
What SMTP settings must I use in Manager?

@bartona, you need to check this with your email provider. But your SMTP hostname is more likely than not to be smtp.btinternet.com. And your username is more likely to be suesew rather than the full email address.

@Andries, your username is more likely than not to be info than your full email address. Note, however, that this username should be the one you log into your email account with. Is that really info?

The information is correct, it should be mail and not smtp as shown form the website settings here:-

IMAP settings

Incoming Mail Server : mail.btinternet.com

Port : 993 (this should be automatically populated by selecting the SSL encryption)

SSL Encryption : Enabled (but not STARTTLS)

Username : your email address including the @btinternet or @btopenworld.com part

Password : your btinternet or btopenworld password

Root folder/path :

Folder separator : . (full stop)

Please do NOT enable “secure password authentication” (SPA). It’s not needed when you use SSL encryption and won’t work.

If your IMAP client supports it, we recommend you also set up the following folders:

  • Trash
  • Sent Items
  • Drafts

POP3 settings

Incoming Mail Server : mail.btinternet.com

Port : 995 (this should be automatically populated by slecting the SSL encryption)

SSL Encryption : Enabled (but not STARTTLS)

Username : your email address including the @btinternet.com or @btopenworld.com part

Password : your btinternet or btopenworld password

POP from folder : by default, POP will pull emails from your inbox

SMTP settings

Outgoing Mail Server : mail.btinternet.com

Port : 465 (this may not be automatically populated on selecting SSL, so you’ll need to check)

SSL Encryption : Enabled (but not STARTTLS)

Authentication : PLAIN

Username : your email address including the @btinternet or @btopenworld.com part

Password : your btinternet or btopenworld password