Hello. I have been experiencing this problem for a while now with the new Outlook.

Many times I have been sent an email from family or friends and I don't receive it. they may send the email a few times before it shows up in my inbox and sometimes it will show up multiple times after a few tries.

I have also had this problem when requesting activation emails when registering for accounts on sites too. usually I do not receive the email in my inbox and I have to contact the site customer support. On occasion I have requested the email to be sent more than once and again, after a few requests it may finally show up in my inbox, but multiple times.

I understand that emails may take a little while to show up but sometimes wait over an hour and the email still does not arrive. I am currently waiting for an email since yesterday and i know it will not arrrive yet I have no option to ask for another one! it is very frustrating.

Until Hotmail switched to outlook I never had problems with receiving emails and I would receive them instantly. 

Please advise me on how I can fix this problem as my inbox settings are all correct. I have already read other support answers and have checked to see if this will fix my problem but it has not.