Hotmail (Outlook.com) Emails Not Arriving? How to Fix Free Email Delivery Problems

Have you ever had an experience like the following?

• An email you were sure you sent never reached the recipient
• An email that should have arrived never came

(↑ These are really the same thing, just from opposite sides.)

In such cases, it is highly likely that the email disappeared somewhere between sending and receiving.

Among free email services, some deliver almost reliably, while others fail to deliver quite often.

We hesitate to criticize any single service, but unfortunately, Hotmail has a high number of problems with emails not arriving or disappearing.

(Note: Microsoft’s Hotmail is now Outlook.com. Addresses ending in @hotmail.com, @outlook.com and @live.com are all handled by the same Outlook.com service, so the advice in this article applies to them as well.)

We often communicate with clients by email, and there have been several cases, particularly with clients using Hotmail, where we lost contact with them, or where clients called us to say “we haven’t heard from you” even though we had sent them emails.

Hotmail is an email service provided by Microsoft, but it seems that for more than 10 years it has been unable to identify the cause of emails not being delivered.

If you are concerned, or if you need to use free email for important correspondence, it may be somewhat more reliable to avoid Hotmail and use a different service.

We explain why below.

To combat spam, each email service uses a “blocklist” that determines which email addresses to block. If an email gets caught by it, it may be blocked and bounced back as an error, or it may not be received properly.

Hotmail in particular seems to have overly strong (?) spam filtering and tends to block even emails that do not need to be blocked.

You might wonder whether, if there is a blocklist, you can also set up an “allowlist,” but that is not the case: apparently Hotmail has no way to exempt specific senders from its blocklist.

In other words, unfortunately there is nothing email users can do to fix or prevent emails they cannot receive.

If you have used Hotmail for many years and feel that creating a new email address now would be too much trouble to manage, we recommend keeping the following points in mind.

When an email you are expecting from someone does not arrive, or you are supposed to get a reply but hear nothing:

1. First, check that the email address is correct
2. Check whether it has been filtered into your spam folder
3. If you still cannot find it, it has most likely disappeared somewhere along the way, so the surest approach is to change your method, for example by contacting the person again from a different email address or confirming by phone.

If you follow the steps above, you should be able to avoid important emails never arriving or losing touch with important people!

We are considering measures within our company to minimize cases where our valued clients’ visa matters, or the inquiries they have kindly sent us, disappear without ever reaching us. However, because of the mechanism described above, we cannot completely prevent some emails from being unluckily blocked or not received.

We make it a rule to reply to emails from clients within two business days at the latest. If you are one of our clients and have not received a reply you were expecting, our email may have disappeared for the reasons above. In that case, we would appreciate it if you could contact us from an address with a different email service, or confirm with us by phone.

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