TIPS & MYTHS
Why you shouldn’t use them for your job search.
SUMMARY:
Do you tell prospective employers to contact you at an Outlook.com, Hotmail, MSN.com, or Live.com e‑mail address? If you do, there’s a small but real chance that Microsoft will block a given employer’s e‑mail if they respond to yours. You’ll never know they answered your e-mail. The employer may never know that you didn’t receive their e‑mail. Even if they find out, they’re not likely to make any further effort to contact you.
THE STORY:
This is a problem only with Outlook.com, Hotmail, MSN.com, and Live.com—all of which are owned by Microsoft. This can affect all e‑mails sent to Outlook, Hotmail, MSN, and Live e‑mail addresses—not just responses to job applications. No other e‑mail services arbitrarily block e‑mails from other reputable e‑mail services or ISPs like this. This has been going on with Microsoft e‑mail services since at least 2003. It seems to have gotten worse since about 2012. Microsoft’s changeover to Outlook.com (in 2013/2014) didn’t have any effect on this problem.
The e-mails that are blocked are legitimate e‑mails. They’re not spam, they don’t come from suspicious sources, and they aren’t being transmitted through suspicious e‑mail services or ISPs (Internet Service Providers). The sources and ISPs are not on any of the blacklists used by IT security firms to identify spam sources. Only Microsoft is blocking these e‑mails.
A large number of reputable, long-established ISPs and their customers have been affected. These include major ISPs such as Comcast and GoDaddy.
All of a sudden, an entire company (in one case, an entire university) finds that e‑mails sent to people with Outlook, Hotmail, MSN.com, or Live.com addresses aren’t getting through. Sometimes the sender gets a bounceback message. Sometimes they don’t even get that, so they don’t know the e‑mail was lost.
What this means for you is that if you contact a prospective employer using your Outlook.com, Hotmail, MSN.com, or Live.com address, it’s possible that the mail they send back to you will be blocked. This is an especially serious problem for job inquiries. That’s because if an employer who sees that e‑mails sent to you are bouncing, they will probably make no effort to re-contact you. Sometimes the employer may not even be notified that the e‑mail bounced. Even if they do re-contact you, the same problem will recur at every stage of the hiring process, with every person from that company who e‑mails you.
This isn’t happening to everyone with an Outlook.com, Hotmail, MSN.com, or Live.com address. But it’s happened to a lot of people, it’s been going on for a long time, and there’s no reason to expect it to change soon. With all the trouble you take over a job inquiry, with all you’ve got riding on it, why take a chance with something like this?
The problem is definitely at Microsoft’s end. There is nothing you can do about it, except to use another address for e‑mails, an address that isn’t managed by Microsoft. There is nothing that the employer can do about it, and if there were, there’s no chance that they’d take the trouble. There is little or nothing that the ISPs and non-Microsoft e‑mail services can do about it. ISPs are constantly contacting Microsoft about this. Each occurrence of the problem is eventually fixed, but Microsoft is very uncooperative, they can take a very long time to fix it (weeks, often months), and the problem constantly recurs. Microsoft has claimed that there is a simple technical solution that ISPs can use. But it obviously never worked very well in practice.
Microsoft says that the blocking is caused by false alarms from their spam-detection systems, which automatically block certain servers used by various ISPs. Microsoft acknowledges that they’re false alarms. Nobody else’s spam-detection systems have this problem. Since the same problem has persisted since at least 2003, it obviously reflects either a deliberate policy of Microsoft, or an astonishing degree of technical and organizational incompetence over a long period of time.
SOLUTION: I strongly recommend that, if you use a Hotmail, MSN.com, or Live.com e‑mail address, you switch to using a Google Gmail address, at least for your job search, and for other critical e‑mails to total strangers.
It’s also handy to have a backup address in case there are problems with your main e‑mail address.
I don’t like Google much, but to the best of my knowledge, Microsoft has never blocked mail sent from Gmail addresses. Others who have looked into this problem say the same thing. Apparently even Microsoft doesn’t dare mess with that large a user base.
I recommend Google’s Gmail for employment e‑mails. You can, of course, use an independent ISP instead of Google for your e-mails to people and organizations with whom you have an ongoing relationship. (I do this.) But you have to choose your ISP carefully. Some ISPs actually are notorious spam hosts, and get blacklisted (blocked) accordingly, and not just by Microsoft. So e-mails to you from prospective employers may not be blocked, but your emails to prospective employers may be blocked by the employer’s e-mail system. (See “Choosing an ISP”, below, for more on this.)
I don’t recommend Yahoo (remember Yahoo?) because they have occasional problems of their own. But if you’re already using a Yahoo address, there may be no urgent reason to change. If you have an AOL address, keep in mind that this dates you—AOL e‑mail hasn’t been a popular thing for a long, long time. (And I wrote that last sentence in 2008. AOL has been part of Yahoo for a long time now.)
(Another thing: When choosing your new e‑mail address, pick something professional-sounding that is appropriate for use in e‑mails to potential employers.)
Don’t take my word for it:
Do a Web search for the following phrase:
Outlook.com, Hotmail, MSN.com, Live.com reject e-mails
Or try the following phrase (include the quotation marks):
“Reasons for rejection may be related to content with spam-like characteristics”
(This wording is from Microsoft’s standard bounceback message.) You’ll see many postings by IT people discussing this problem. It was still going on as of 2018, and it’s still going on in 2023.
There’s a 2014 thread on this at webhostingtalk.com, an interesting hosting-industry forum.
In 2007, Dan Goodin, an internationally-recognized IT security expert, wrote an article about this in The Register: “Hotmail’s antispam measures snuff out legit emails, too.” It’s exactly the same thing that is occurring now.
Back in 2003, CNET reported on exactly the same problem: “MSN blocks e-mail from rival ISPs.”
CHOOSING AN ISP FOR YOUR WORK-SEARCH EMAILS—AND YOUR WEBSITE (useful info, and perhaps hard to find): As I said, Google Gmail is the simplest solution to this. But if you’re looking for an ISP (or hosting service) to host your website or for private e-mail service, do your homework and make sure it’s a reputable one. ISPs that host a lot of spam-generators are likely to be blacklisted, so that e-mails sent through them are blocked—and not just by Microsoft. And cheap or free e-mail hosts (see below, on EIG/Newfold) might make their real money by spamming you, pushing ads at you, selling the information you provide, and wasting your time with efforts to hook you onto signing up for features that cost money. In the hosting market, the better-known names are not always the best.
Crystal Résumés has used MDD Hosting for web hosting and e-mail since 2016, and we recommend them highly. They seem to be one of the best-known and best-regarded independent hosting services.
A tip for weeding out the usual suspects: For a long time, a surprisingly large number of hosting firms—big, medium-sized, and medium-small, including many well-known names—were owned by a company called Endurance International Group (EIG). EIG did not have a good reputation, and the quality of service at the firms they acquired was said to fall off badly post-acquisition. EIG merged with Web.com in 2021 to form Newfold Digital, one of the world’s largest web-hosting providers. Newfold seems to have the same reputation that EIG had. (See, for example, thishosting.rocks, List of All EIG (Newfold Digital) Hosting Providers and Why You Should Avoid Them, which I checked in March of 2024.)