Calling MSN Windows Live Assistance - Hotmail was very tricky because, despite the name, it's clear that Microsoft works hard to avoid providing live assistance. In fact, throughout the call, I was told several times to get help from online support. This counteracts the entire point of having a live assistance number and frankly was frustrating. Equally frustrating was the fact the automated system was very sensitive and would stop if it thought it caught a word in the background. I quickly realized I'd have to take it off speaker which made calling even less convenient. 

While it was sensitive, it wasn't appropriately responsive which made it even more difficult to deal with. When I first called it thanked me for calling Microsoft, then recited the standard messaging that the call would be monitored and potentially shared. The automated voice message then said, "To help us best assist you, I need to know if you're calling as a home user or a business user." I said home user. 

Then, it said it looked forward to assisting me today and asked what it could help me with. There was an awkward pause and I realized that it was waiting for me, so I said "retrieving my Hotmail account." It asked me how it could help me with my Hotmail account so I repeated the same thing. It was odd because it did not instruct me to say in a few words what I needed or anything like that. It would just stop talking and the blank space would awkwardly prompt me to say something. 

After I said that a second time, it said okay, but then quickly ran through a list of things so quickly that I didn't understand what the options were. At the end of the options, there was another awkward pause so I attempted to say "Repeat the list", but it didn't work.

Instead, after another lengthy pause, it told me that Microsoft support was now online and that I could go visit it at https://support.microsoft.com/.  It repeated the web address a second time and offered me the option to have it texted to me so I could access it more easily. I said no because I was still waiting to talk to someone and I knew there were options that I had missed earlier such as account support and forgotten password assistance. 

While I was hoping I'd be directed there, instead the message simply said, "Okay, thank you and goodbye." I was a little shocked it just hung up on me like that, but also frustrated because, after five minutes and two phone calls, I was no closer to actually getting any live assistance.