Why I have to leave hotmail. A not so simple explanation.
The simple explanation
Don’t worry, this isn’t on political, religious or charitable reasons. The reason is quite simple, I’m blown away at the volume of emails that aren’t getting through to me. Not getting redirected to junk, but literally thrown aside at Microsoft’s’ discretion at any given time without notice given to the sender or the (non)recipient. What follows is a long and detailed account of how I came to realise this issue existed, as well as my ultimately futile exploits to resolve the matter. There’s no need to read them all, unless you feel compelled, but I do urge you as one email user to another – if you use hotmail: change supplier for your own sake as well as people trying to contact you.
I’ve been a hotmail user for as long as I’ve had an email address. To this day, I still use the same email address I used when I first signed up in secondary school. This hotmail address was my primary email and has been until today. So it genuinely pains me to change things up, but I have completely exhausted all other options. This post is a means to try and explain the problem, my multiple attempts at fixing the issue and Microsoft’s belligerent and arrogant responses to my heart-felt desperation to fix the problem.
I would urge anyone using hotmail addresses (this includes any emails containing the following; @hotmail, @live, @msn, @Microsoft, @outlook or @Skype) to seriously consider moving services across to another provider. Generally speaking, the much better alternative is Google Mail(Gmail) anyway.
The not so simple explanation
The problem of not receiving emails had been present for a very long time. But naturally, as a user of one of the world’s most well-established Webmail softwares, the obvious culprit to missed emails that never arrived was clear – sender error. So over the years that had been my most common assumption towards such occasions.
It wasn’t until late last year I realised something that a lot of the websites I managed suffered from. Any email sent from their domain would automatically be sent to my hotmail junk folder. Not a big problem, but it was intriguing when considering that some of these domains, websites and housing packages were only days old – and yet Microsoft had already labeled them as potential threats to my hotmail account.
I wondered if, over time, hotmail would learn these sites to be safe, so instead of adding the addresses as contacts, I would often wait to see if Microsoft ever picked up on the safer nature of the emails. Much like their junk mail filter terms outlines. In fact, it advises senders not to worry, since their algorithm is constantly renewing and refreshing.
Soon after this realisation, it would become common practice for me to check my junk mail inbox as I would my inbox. To my shock and horror, many highly important emails are redirected there by Microsoft’s ‘clever’ and completely automated algorithm.
In March of this year, as my e-commerce website states to take-off in a big way, I needed to upgrade my hosting package for my website . For the non-tech savvy, hosting is how the website is stored online. I needed to change from a shared server (online computer) to a dedicated one. Made sense for security and for site performance. You can rest assured, that having purchased many of these for calls clients of mine over the years, I knew what to look for and what to avoid. But upon finally selecting a secure server of my choosing, a trusted hosting company went ahead and set up my brand new website server. Fresh. New. That means new hardware, new software and a new IP addresses (unique location of the server). Before too long, the new website was live on the new server.
It was business as usual. But faster and more secure. Until I noticed something. All my customers with hotmail addresses weren’t receiving order confirmations or any of our emails. Based on the problems that previously existed, I naturally urged the concerned customers that phoned up to simply ‘check their junk mail’ and ‘we’ll and it again’. But something odd happened when I ran my own tests. The emails didn’t come through to hotmail addresses. Not to junk. Not anywhere. What was extra unusual was that there was no bounce-back email to the sender or to the intended recipient. Very odd.
Naturally, since the only thing that has changed was the server, my first instinct was to work with the hosting company to fix the issue. And we worked hard. They literally did everything that they could before ultimately concluding that this was a Microsoft problem. And here’s why; the emails are leaving the server fine. The emails were being received fine by Gmail, Yahoo, and every other domain extension under the sun. They weren’t even going to junk. But mysteriously, Microsoft has decided that this brand new server was a threat so big that it automatically disposed of any references to them.
I struggled to believe this at first. Why would Microsoft so that without at least telling the website owner that their website had been essentially blacklisted by their services exclusively? Especially when you consider that the content of our emails are about desktop toys. Lego minifigures. There is literally nothing in these emails that could be taken the wrong way. And I know this because that was my next step: approaching micros. I needed to know why my emails were getting blocked.
So that’s what I did. I pursued as many tutorials and Microsoft-published articles as I could to try and better-conform my emails and website to their standards. And after following all (and, believe me, it was a massive list of extremely generic instructions), I messaged Microsoft asking why my emails were still getting blocked by Hotmail addresses.
They offered me extremely generic responses, linking me back to the very articles that I had explained I had complied to. After several exchanges via live chat, I was asked to speak to someone via a live phone call at 7pm on a Saturday (the next available slot from the ‘next tier’ of technicians).
So, even though it interrupted my weekend, I awaiting the phone call which came through at 8:08pm. But, by this time, I was just glad someone would be willing to hear me out and hopefully solve the problem. Although friendly, the phone call concluded very quickly that they would need to put me through the third tier or technicians for further assistance. I was told that they would email me on the Sunday and that I would receive a phone call later that day to make sure everything had been sorted.
I left that phone call thinking there was light at the end of the tunnel, but upon receiving the same generic email from before the phone call, I realised I was just being passed in circles. There was no follow-up phone call and all subsequent emails were templates outlining the same articles on how to ‘better comply’ with Microsofts’ magic algorithm. So magic, in fact, that there is nothing they can do to change or help someone who is inexplicably being blocked.
So, three months, 18 emails, countless chat windows and one phone call I was back at square one, and to this day – I remain in the same state as where I started. Microsoft could not care less that it has effected my business and increased my workload by 50%. For work, I now have had to sign up a business hotmail account that is used exclusively for emailing other hotmail customers. Since that’s the only way the emails will get through.
Sickened and totally exhausted after trying literally everything to fix this issue, I am left with no other options for my business. But when it comes to my personal emails, I can make a decision to move away from Microsoft permanently. Aside from boycotting the company who caused me so much hassle, there is a more serious reason – I don’t want Microsoft deciding which emails I receive and which ones I don’t.
So I will no longer be using my hotmail accounts, if you wish to reach me – do so at firstname.lastname@example.org.
I’m not looking for a mass-exit of the technology giant, I think that would be pointless. But I would urge all hotmail users to consider switching after learning what I have about this service.