Outlook 2007 not sending mail after installing the Hotmail Outlook Connector

  ria 16:50 11 Nov 14

I have been using BT for my emails for years now and never had problems using their yahoo.co.uk for web-mail and outlook 2007 on my computer. Following BT not using yahoo anymore and now just using BT Mail I installed the Hotmail Outlook Connector, so I can use outlook.com as web-email. I created a Mapi account in Outlook and copied all my contacts into it. I also created some additional send/receive e-mail addresses in outlook.com, they are BT sub accounts. They are showing up in both outlook.com and outlook 2007. The problem I have that outlook.com and outlook 2007 will not send emails. They either are stuck in the outbox or they come back with the following messages. The first one tells me "not to resend" as the mail is delayed. 1. FW: Delivery Status Notification (Delay) Subject: Delivery Status Notification (Delay) This is an automatically generated Delivery Status Notification. THIS IS A WARNING MESSAGE ONLY. YOU DO NOT NEED TO RESEND YOUR MESSAGE.

Then I get delivery report saying the email cannot be delivered. 2. This is an automatically generated Delivery Status Notification. Unable to deliver message to the following recipients, due to being unable to connect successfully to the destination mail server.

Alternatively, I get 3. This is an automatically generated Delivery Status Notification. Delivery to the following recipients failed.

I have no problem receiving emails. It is not just btinternet.com email addresses, it can be anyone i.e. [email protected], [email protected], [email protected] and so on. I have tried different outgoing server (set as 110 now) settings, like 465 and 587 and 215.

I have been trying to solve this for the past 3 weeks now and run out of ideas, very frustrating. Any help would be really helpful and great.

  Woolwell 17:31 11 Nov 14

If you have installed Outlook connector then you are not using outlook.com via webmail but are using Outlook 2007 for it. Webmail is through your browser. You should not be having any problems sending via the browser. You can also log into BT using the browser and send.

But coming back to your original problem I'm not sure why you set up a MAPI account or how you did it and the problem may well lie there. Suggest that you delete the hotmail/outlook account in Outlook and start again. You can back up the received emails first. The Outlook.com account should be an Exchange Activesync type.

  ria 19:41 11 Nov 14

This all started when I got my new windows phone 8.1 and I wanted to synchronise my contacts and calendar from Outlook on my PC to my phone. I followed the instruction on: click here

  Woolwell 19:58 11 Nov 14

You probably do not have an exchange account. I would have set up an Outlook.com account on Outlook 2007 see Office support. That should then sync your contacts and calendar with Outlook.com. Your phone with an Outlook.com account should then pick up the contacts, etc. This is how I sync between my W7 desktop and W8 laptop.

  ria 20:13 11 Nov 14

I followed the instructions to use Outlook without Exchange as it said: this is typically the case if you use Outlook at home

  ria 20:23 11 Nov 14

Looking at your link....How often does a "HIP challenge" appear when you send an image? Every time?

  Woolwell 22:48 11 Nov 14

Hip challenge? Never come across it.

  ria 18:35 12 Nov 14

The Outlook Connector uses a Human Interaction Proof (HIP) challenge. A HIP challenge uses an image or audio file containing characters that are decipherable only by a person. This requirement confirms that a person, rather than an automated program, is trying to send an email message. This helps prevents automated programs from misusing the Outlook.com service.

On occasion the HIP challenge will appear after you send a message with your Outlook.com account.

Note There might be a delay of a few seconds or longer before the HIP challenge appears. If the message you are sending is not in your Outbox but is in your Sent Items folder, then your message has been successfully sent to the Outlook.com server.

  Woolwell 21:25 12 Nov 14

Interesting never seen it but rarely send from my outlook account. I mainly use the account to sync calendar and contacts.

  Woolwell 21:26 12 Nov 14

Just sent a test image attachment and no HIP challenge.

  ria 09:03 13 Nov 14

Ok, thank you. Does outlook.com sync automatically with outlook desktop or do have to do it manually?

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