Hotmail keeps bouncing my emails

Are you having problems between your cool email service provider and corporate email providers?

For the purpose of this explanation, a “cool email provider” is a provider listed as signatories of the statement on Data Retention on this page:

https://lists.aktivix.org
or here:
https://help.riseup.net/en/security/resources/radical-servers

You will be warned about a certificate in a scary way, telling you this site is NOT to be trusted! You will need to indicate that you “understand the risks” and accept it, for at least this once. It is part of the tension between corporate things and cool things.

This is the robot portrait of most instances of big email providers blocking cool email providers:

As most email problems, its root is spam. Emails sent out by advertisers in order to get you buy their products. It is widely accepted that about 95% of all email traffic in the world is spam. If it did not work as a marketing took, companies would not use it.

A spamming agency (a business, with full time staff doing this for a living) sends an email to as many users as they can, from as many email service users, pretending the service providers’ administrators, and requesting their user name and password.

No matter how many times cool email providers’ real administrators send newsletters to all users saying they will never ask for this information, there is always one – at it takes only one – who answers to such requests and gives their user name and password to the spammer.

The spammer then uses this user name and password to send out spam – thousands, maybe millions of emails – to as many addresses as they can. Usually they have “harvested” these addresses from websites and mailing lists. There is actually a market for databases of valid e-mail addresses and it is the job of other full time workers to build up such databases, which are then sold and made available to the full time workers mentioned above who use them to spam away.

Most of this spam gets trapped in anti-spam measures installed on e-mail servers. In fact, most e-mail servers manage to filter out most of the spam they receive, using certain measures, and programs installed on the e-mail servers themselves.

One of such measure is to “block” addresses from where previous and known spam has originated. There are companies that maintain databases of IP addresses that are known to send out spam. This is why spammers need to “phish” new IP addresses; because when they send spam from their own IP address, that IP address becomes known as spammer, the receiving servers report it as sending out spam to the spam databases and the servers using those databases block that IP address to avoid receiving spam from that address.

Then spammers move on to another IP address, sending emails using the user names and passwords that they have phished, i.e. pretending to be that person sending spam, and effectively sending the spam from an IP address not previously known as spam-sender. But after this spam is sent from this cool e-mail server, its IP address is placed in the “databases of spammers” and it gets blocked as well.

Of course most of the email addresses receiving the spam are hotmail, yahoo and google addresses, because most of the email addresses that exist in the world are hosted in those big corporations. And of course they use anti-spam measures, including blocking IP addresses listed in those databases.

It is not only cool e-mail servers that suffer phish attacks. As mentioned above, spammers are companies with full time staff. Who value a cool e-mail address as much as a google email address. The important thing is that it allows them to send spam without using their own server or their own IP address, so some one else gets blocked, not them. When any e-mail server appears as the spam sender and gets blocked by the rest of the servers, in most cases, the administrators quickly find out which account got compromised, they block that one account and the spamming stops. They then report to the databases where they are listed as spam, and when the database maintainers are satisfied that no spam is coming from their servers any more, they remove them from the databases. Then the rest of the servers normally accept email from those servers again as they are not listed as “spamming servers” any more. If, say, google administrators for instance, notice that hotmail is taking too long to accept their emails, they can contact hotmail administrators directly. When it is google contacting them, hotmail has a reason to react quickly: co-operation between big players is useful, profitable and necessary.

Most cool e-mail service provider have a user base that is a fraction of gmail’s or hotmail’s user base. For gmail or hotmail, co-operation with small service providers is not that vital.

So emails coming from your cool e-mail list can be blocked by hotmail for long periods of time without hotmail’s revenue being affected. Small service providers are really too small for a full time administrator under pressure to bother.

Capitalist structures and needs then create a breakdown of communications between corporate and cool e-mail providers. Cool e-mail servers talk well amongst each other, and the same happens between the corporate ones. Which makes the solution in the medium to long term to bring the people you want to communicate with by email, to the email providers you want to use.

In the short term, you can check directly with your email providers what your current problems are due to: for riseup:
https://status.riseup.net/
You will also be strongly warned about a certificate, like with aktivix.
If your provider is aktivix, at the bottom of the page above there is a list of ways in which you can contact the administrators.

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