Outlook 2007 not sending mail after installing the Hotmail Outlook Connector

  ria 16:50 11 Nov 2014

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.

  ria 19:41 11 Nov 2014

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

  ria 20:13 11 Nov 2014

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 2014

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

  ria 18:35 12 Nov 2014

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.

  ria 09:03 13 Nov 2014

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

  ria 18:04 19 Nov 2014

I am back again :-(( I still can not send e-mails in outlook 2007. The e-mails, contacts and calendar are all syncing fine, I just can not send any e-mails. They all come back about 24 hours later. I did as you said and deleted the hotmail/outlook account in outlook 2007. When I created my account again (the same one as in outlook.com), it recreated it as an MAPI account. All I have now in outlook 2007 is this account.

  ria 18:58 19 Nov 2014

Yes I have, even printed out instructions and followed them to the letter. I have not got an @hotmail.com or @live.com account. Mine is a [email protected], does this matter?

  ria 10:34 20 Nov 2014

I really don't understand. The only account I have got set up in outlook 2007 is the account I set up with the Hotmail connecter. It's an MAPI account which has the same username and password as my Microsoft account and my BT e-mail account i.e. my [email protected] Everything is synced between Hotmail.com and my phone and all emails download into outlook 2007, but I cannot send emails in outlook 2007. They either get stuck in the outbox or come back as undelivered after 24 hours.

  ria 14:32 21 Nov 2014

Yes, in outlook.com and outlook 2007 with my BT address. The emails get send with no problems in outlook.com, but not outlook 2007.

This thread is now locked and can not be replied to.

Elsewhere on IDG sites

Huawei MateBook X Pro (2019) review

Magical mystery tour - Artist colourfully customises bus to promote positive mental health

Apple Streaming Service Release Date & Apple TV Subscription Rumours

Quel est le meilleur iPad ?