top | item 38790854

Outlook/Hotmail is no longer blocking my mail server

196 points| unclet | 2 years ago |taoshu.in

250 comments

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huhtenberg|2 years ago

We go through this every few months. Here's the recipe -

1. Visit https://olcsupport.office.com/ and submit the complaint.

2. Wait for the auto-reply, followed by the "Nothing was detected" email.

3. Reply to the latter with "Escalate" in the body.

Within a day, they hammer shit in place and the block is removed.

wolverine876|2 years ago

Do they ever respond? Maybe the block comes and goes, and has nothing to do with attempts to contact Microsoft?

RankingMember|2 years ago

Really love the modern support experience of no-response, trial-and-error, until suddenly, if you're lucky, the void on other end magically solves the problem. Confidence-inspiring stuff

albertgoeswoof|2 years ago

I run a small transactional email provider (https://mailpace.com), our IPs are very rarely added to blocklists- but we are very strict on what we allow through our service, and surprisingly we’ve had no long term delivery issues with any of the big providers.

So thanks to the federated/decentralized design of email, is totally possible to be part of the network without any special privileges.

We are sending millions of emails every day though, which is quite different to sending a couple hundred personal emails a week. If you’re running this on a cloud host, expect to be blocked by default. However if you can find a small vps provider you’ll have better luck on sending yourself.

yonrg|2 years ago

Right. When I changed my vps to another hoster, I totally forgot how much trouble it was to get a good reputation in the beginning.

But it was really not that much work again. Just unfortunate, because one big Mail provider just discarded instead of rejecting my mails. After this was settled, everything works quite nice again. Important to me is keeping spf, dkim, dmarc and now also mts up to date. See mail-checker.com e.g.

I still wonder though, why some big mail providers do not do dkim/dmarc? I happen to realize this when I started to fight spam and gave incoming mails without dkim/dmarc a high spam score.

jabart|2 years ago

We host in a datacenter and sending from their IPv4 or our own /24 IPv4 block has no issue. We also have the volume to keep things going as well to build up the reputation.

amar0c|2 years ago

Can I use you as relay to my Postfix for 'regular' emails ?

TobyTheDog123|2 years ago

(Unrelated to the OP - but I've been so frustrated by this for so long that it's worth the [flagged])

A product like this is exactly what I've been looking for with pretty great pricing.

The one thing that this (and most providers) are missing is making email easy to test. I'm about to launch a product where email is critical, and there's no way to send an example email (with a non-test email address) to your service and see that you receive it, without it being sent to the To address.

Better yet, the few providers that do support it charge as if it were a real email, when none of the delivery costs exist on their end (there are infrastructure costs, sure, but there is none of the reputation risk nor need for clean IPs, the reason people use transactional services like these in the first place).

shaicoleman|2 years ago

Outlook/Hotmail blocks DigitalOcean. After half a dozens attempts over the years to delist my IP, and following all the best practices (dedicated fixed IP, SPF, DKIM, DMARC, FCrDNS, zero spam, TLS, etc.) I gave up.

Eventually, most people realize that their Outlook/Hotmail email service is defective because they're not receiving emails, and they migrate to another email service.

Avamander|2 years ago

> Eventually, most people realize that their Outlook/Hotmail email service is defective because they're not receiving emails, and the move to something else.

Or people realise that DO's current anti-abuse is very insufficient and will move to something else.

huhtenberg|2 years ago

I have a personal mail server and I too had no choice but to blacklist DO.

They generate a lot of phishing emails (rather than conventional spam). I used to diligently report it to their abuse contact, but they don't seem to care or do anything about it in the slightest.

rixthefox|2 years ago

> most people realize that their Outlook/Hotmail email service is defective

This is exactly what I've begun telling people and warning friends and family members about. I run my own email... well I run my own ISP at this point and we have our own dedicated block of IPv6 addresses but still rely on IPv4 addresses from our cloud providers and I've started to grow frustrated by the lack of movement by the incumbent email providers that I've started just straight up telling people don't expect any email delivery from me if you're using any provider that still lacks proper IPv6 on their SMTP servers.

It's no longer my problem and I will happily tell people that their email provider is defective and that they need to find a new host. If that is too much for them, to bad so sad not my problem. I did everything I could do. At some point you have to stop trying to work around "Big Cloud" and their nonsense.

WarOnPrivacy|2 years ago

> Outlook/Hotmail blocks DigitalOcean.

Microsoft blocking a mail server and DO being blocked aren't necessarily the same thing.

I service a number of MS accounts (hosted domain and O/H/live.com) and they block mail from small servers I manage - and from (non-major) online services I work with. There are forums frequent that send verification mails to MS addys that never arrive.

Past that: My last time blocking mail server attacks from DO IPs is today. It's always today and has been years and years. Not just DO. OVH, Psychz and a at least doz more attack with that consistency.

[edit: Post below mentions DO SMTP changes in 2022. DO is still attacky but less attacky is possible. Not sure.]

And not that far behind, Amazon. Amazon is a lot harder because unlike the above, I regularly get legit traffic from them.

vel0city|2 years ago

I've had decent deliverability to some of my Outlook addresses from my Digital Ocean droplets for about a decade. Low volume (a dozen or so a week?), only to a few dozen addresses. I had poor deliverability until I updated the Reverse DNS to match my sending hostname. Since then, I have not had a single email get filtered.

tempnow987|2 years ago

Or folks will check where their spam comes from. At least 2-3 years ago digital ocean was a ridiculously major source of spam. I've no interest in investigating why, but there is a near zero chance they were following anything like "all the best practices".

This is from DO's own site based on a quick search:

"I am being BOMBARDED, and I mean BOMBARDED with spam from Digital Ocean over 5 spams a day all from the same bunch of domains, all hosted on DigitalOcean and coming from your IPs.

In the last 2 weeks I’ve emailed your abuse mailbox 20+ times and filled in the contact abuse form 10+ times.

NOTHING is being done about it. My next plan of action is to keep posting here until Digital Ocean takes action.

Do you even have an abuse team? are they doing any work at all? I can provide 30 more samples if needed."

Absolutely pathetic - all major providers should blackhole email from DO.

Note that this contrasts to AWS. I was on AWS from flat network days (where folks were running scans internally etc. AWS respond with a ticket usually to abuse reports and then usually a bit later a note that things have been taken care of.

How does AWS which is FAR larger in IP address space than DO have so much LESS spam coming from their IP address space? Perhaps because they pay a tiny bit of attention to the issue.

dangus|2 years ago

This probably isn’t directly helpful or relevant advice, but I don’t see a good reason to spend double on DigitalOcean droplets compared to what you get with Hetzner Cloud.

Aerbil313|2 years ago

Oh, are you the creator of Colemak?

StayTrue|2 years ago

I had this problem for years. I would get the block lifted and it would return in short order. I surmise it’s because my mail server runs on a VPS and other users on my subnet are not well behaved (actually I know this for a fact).

I solved the problem by paying for a next hop SMTPS server as an upstream smarthost for non-local mails. That means my mails come from a subnet that fronts TONS of other servers/domains. That makes it a bigger headache for MS to block.

Sad but there you go. I do not use the external service for inbound. Inbound mails come direct to my server per the MX.

deltarholamda|2 years ago

I do the same thing, also with mailgun. It's generally much easier to deal with, especially if you have a fairly low volume of outgoing emails.

Mailgun has been very good to me, highly recommended.

jbotz|2 years ago

Who do you use for the upstream smarthost?

abberation|2 years ago

Wow, Outlook actually tells you they blocked you? My email (custom gmail domain btw) just ends up in the Spam folder of outlook clients with no notification at all.

delusional|2 years ago

That's a different issue. You're usually not notified of spam designations, but bounces (where the mail server completely refuses to accept your email) do usually receive a notification. If you're designated as both (for example if you keep sending email that bounces) you'll get blackholed and wont receive any bounce notification either.

jraph|2 years ago

I self host. Over the years, I've had both situations with outlook. I've tried many things.

As it happens, I noticed my mails have gone through just fine in the last months, at least to companies using Microsoft services without me doing anything specific, after I threw the towel with Outlook. I did switch VPS providers almost a year ago, though to a provider that I expect to be more filtered (ovh).

sheikheddy|2 years ago

I work on Microsoft's anti-spam team, AMA!

csnover|2 years ago

I guess my question is can you please fix your braindead blacklisting?

Several times per year—I can practically guarantee it’ll happen sometime in December, and indeed had to deal with this just five days ago—I end up with a bunch of users whose email notifications stop working because Microsoft have started blocking the entire netrange where my server lives. I don’t have control over other Linode customers, guys! I even wrote extra code to stop sending mail to addresses that start bouncing specifically to avoid blacklisting, so after MS finally processes a blacklist mitigation request, someone also has to go in and re-enable those accounts.

SPF, DKIM, DMARC are all configured; I’ve sent from the same IP address for about a decade; I’ve not once received an email abuse report; mail volume is low (most days, volume does not reach the minimum threshold for SNDS to report data[0]). I’ve never had any other mail provider blacklist my server. SNDS always says everything is OK as I am S3150s. What is even the purpose of SNDS at this point when it lies about what is going on?

[0] P.S. The janky SNDS calendar widget resets the month to the current month every time you click on a date, even if the date being viewed is in a previous month. I don’t have any hope that anyone will ever touch SNDS code again since it was clearly designed in the early 2000s and the copyright on the site is now ten years old, but this is a pretty silly bug.

Sarp402024|2 years ago

Here is the issue that most ESPs are facing.. Every 5-6 months something is being enabled or not from Outlook's side which affects either IPs or the domain name of the sender and messages land in Junk folder or in quarantine zone. Now, I do know that the IPs might be affected by complaints or spamtraps, or maybe the client sent something suspicious, but trust me most ESPs don't allow those messages to be sent. Also, when the IPs appear GREEN in SNDS, and SPF/ DKIM and DMARC are a part of DNS authentication and headers appear like this: CAT:HSPM;SFS:(13230031)(4636009)(451199024)(7596003)(356005)(7636003)(86362001)(450100002)(8676002)(1096003)(14286002)(34206002)(5660300002)(336012)(26005)(42186006)(9686003)(33656002)(83380400001)(7846003)(33964004)(564344004);DIR:INB; X-Microsoft-Antispam: BCL:0; X-Microsoft-Antispam-Message-Info: You are expecting that quarantine zone is the last place to find a legit message. For obvious reasons I won't share more details, but I bet that from time to time someone is messing with spam filters that can easily result in false positive and angry senders. In any case, especially when we raised tickets to Outlook, at least please inform your team not to reply like robots. If they will share with us the exact reason why a message landed in junk folder that would really help us. If it is the content, we will change it. If it is related with the sender, we will block the sender. If those are complaints, we will block senders and check their subscription sources, but at least we need something especially when SNDS shows Green IP, 0 spamtraps, 0 complaints. Thank you for reading this.

Dunedan|2 years ago

Why do you put mail servers on your block list which never sent spam? And why do you make it nearly impossible to get unlocked once on that list?

TonyTrapp|2 years ago

Similar question as my sibling comments. I have rented a server with a static IP address for over ten years now. Nobody else has used this IP during this time. Yet, every few months I have to beg Microsoft to unblock the IP. In the beginning I could do this on my own, but something changed a few years ago and now I have to beg my ISP (netcup) instead to contact Microsoft on behalf of me to temporarily whitelist the domain. Then wait another 2-3 months and do the same dance again.

Why? Why can Microsoft not learn that an IP has been healthy and spam-free for 10+ years and only bother me when there is actual spam is being sent?

currysausage|2 years ago

The most pressing question: why does Outlook.com just silently discard some emails?

pbhjpbhj|2 years ago

Why doesn't whitelisting an address ensure one receives messages from it, the address has never sent spam, sends at most a couple of emails a day. But I couldn't receive emails from it, there was no notification or information despite the address being on my whitelist?

What's the rationale there?

BLKNSLVR|2 years ago

What kind of tiers are there for filtering?

Eg. Known bad domains, known bad IP addresses, incorrectly setup DKIM / SPF, no reverse DNS, non-matching reverse DNS, and that's before even looking at content to determine whether spam.

NorwegianDude|2 years ago

What's the best way to quickly get MS to trust a server/domain?

Does MS ignore IP reputation in cases where the domain has a good reputation?

How would you go about getting a new domain and an IP address from a public cloud provider working consistently?

I've had issues with outlook when it comes to new domains and IPs, but after some time it works. I do however usually have more email than a personal server so what's the best way - if such a thing exists - for a personal server that has much lower volume of mail to be trusted?

Biganon|2 years ago

How do you sleep at night?

trympet|2 years ago

My penis enlargement pill newsletter isn't showing up in my customers' inboxes. I could have been a penis-enlargement millionare if it wasn't for your stupid spam filter. What to do?

WarOnPrivacy|2 years ago

>When I try to reply his message in my mail client, it received the following error message:

> Delivery to xxx@outlook.com failed with error: outlook-com.olc.protection.outlook.com. said:...

He got error messages? I get mail silently dropped.

MS drops mail from my reputable mail servers - and from rep svs that send mail to MS accts I manage.

Dunedan|2 years ago

After many years of regularly getting blocked by Hotmail and outlook.com, I just decided to reject every incoming email from Hotmail and Outlook with an error message explaining the situation. If they don't allow me to respond to emails sent by their customers, why would I allow them to send me emails in the first place?

unclet|2 years ago

If all indie mail servers blocked by Hotmail block mail from the blocker, it will make the big player review their blocking policy.

Avamander|2 years ago

You sure showed it to them. /s

Did you sign up to their JMRP to figure out what they didn't like or how were they blocking you?

TwoNineFive|2 years ago

I run my own mail servers and hotmail and other Microsoft-based email services regularly blocks my mail by source IP on the various domains I run.

I've been using the same /29 network for over 15 years now. There's no nearby adjacent networks that are on any blacklists.

I monitor blacklists on a regular basis.

No marketing. The domains I run are strictly personal and projects. I monitor volume and all kinds of stuff. I know there's nothing like spam or any kind of marketing going outbound.

It's astonishing how honest Microsoft is when I send them an email telling them to unblock. They literally just admit that they never had reason to block the domain/IP and they unlist it for a few years and then it goes back on their list.

It's become apparent that they blacklist by default.

Fortunately I only run into the occasional idiot who uses Hotmail or live.com.

spoiledtechie|2 years ago

GMail is the worst for email blocking resolutions. They don't have an effective feedback loop built into their system. So when a user does block you, no one is told about it, to be fixed. Therefore lowering your reputation with them over time.

How can we as ESPs respond to them appropriately with removal of these people who don't want our emails anymore, if we don't know who the user is?

If there are any GMAIL service team members here, I would LOVE to know why a feedback loop was never implemented like the other providers.

uxp8u61q|2 years ago

Maybe ask yourself why some users end up blocking you altogether. Surely you didn't start sending them newsletters or the like without being completely certain that they wanted to receive them, and you provide a simple, prominent and reliable way to unsubscribe if/when they change their mind, right?

inetknght|2 years ago

> How can we as ESPs respond to them appropriately with removal of these people who don't want our emails anymore, if we don't know who the user is?

1. Don't send spam

2. ???

3. Profit!

Literally _all_ email that I've blocked has been from companies where I uncheck the box "send spam to me" and the company sends it anyway, or where the company thinks "oh this guy bought stuff from us, we can now send our daily/weekly/fuckly marketing spam!" or "we got your email from whatever shady place, and now we're sending you our information because you're in our industry" or stupid shit like that.

Gmail does not have a "block everything from this domain feature". I would love to block whole domains from my gmail account. Alas, I run my own email server to achieve it.

vouaobrasil|2 years ago

Running a mail server should be something anyone can do. And while this is cool, there are so many other problems to do it. It's the price we pay of letting big tech companies control so much of the virtual infrastructure: big tech has commoditized the internet so much into a platform for consumerism that it becomes a valuable target for spam.

In my opinion, the internet would be much better if none of the big players ever entered it, including Google, Facebook, Yahoo, etc, and it would allow for many more decentralized and valuable commons like email.

thejosh|2 years ago

The main benefit of Gmail and other big providers is the anti-spam, anti-scam, "Google knows best" approach works really well.

When I last helped manage a mail server for a small business (late 2000's) SPAM was an absolute mess. You can really see why Azure etc has consumed on-premise Exchange.

The massive downside is they are the deciders of who gets through their gates, and if you're on their shitlist, goodluck.

mort96|2 years ago

The basic fact of the matter is that >99% of people will never be interested in hosting their own e-mail server, and that's okay.

This means we need organizations to host e-mail for people. In a capitalist system, that means companies, and it leads to consolidation and monopolization. So far, governments have been seemingly uninterested in going after the large e-mail providers for anticompetitive practices; maybe that should change. But as long as those anticompetitive practices only really affect individual hobbyists who wanna host their own e-mail, while business interests are unaffected, I don't see this changing.

helsinkiandrew|2 years ago

> big tech has commoditized the internet so much into a platform for consumerism that it becomes a valuable target for spam.

What? Spam existed long before the big tech was around (admittedly the first Spam was probably from DEC, but before 'big internet tech' existed anyway) - it grew because of the amount of people/consumers on the internet. And credit where credits due: getting rid of spam was very time consuming until Google came out with one of the first effective filters.

haunter|2 years ago

> the internet would be much better if none of the big players ever entered it, including Google, Facebook, Yahoo, etc,

How this could have been possible? Like there must have been some outside regulations in the late 90s/early 2000s. Maybe as an effect of the dotcom bubble?

Also it’s a good theory but doesn’t fit the capitalist picture at all.

brunnock|2 years ago

I ran into this issue several years ago. After complaining, MS allowed me to send email to MS properties (hotmail, live.com), but continued to block my email to their Office 365 clients.

I now use AWS SES to handle mail delivery. It's free for up to 200 daily messages which is fine for me.

tschumacher|2 years ago

Maybe the big webmail providers are relying more on machine learning for filtering spam instead of blocking IP ranges these days.

gumballindie|2 years ago

That would be horribly unreliable. I hope they dont rely on machine learning for such critical infrastructure.

V__|2 years ago

Is this mira of a U.S. centric problem? I selfhost my mail in Germany, have one at a smaller mail provider and never had problems.

It is also not uncommon for companies to either have a local Exchange Server or use the mail service at their hosting provider. If everything is configured correctly, delivery works fine.

psd1|2 years ago

Your experience may not be typical. I ran mail servers before office 365 was a thing, and I often had to get off block lists. There are stories on HN about it being worse, now that you have to request unblocking from MS and Google. Yours is the first comment that doesn't complain.

justsomehnguy|2 years ago

Personal anecdote != universal, global experience.

> have one at a smaller mail provider

    a) [hosted] Mail provider
    b) Server (colo/dedicated/VPS/whatever) provider
Choose one.

> not uncommon for companies to either have a local Exchange Server

Yes and it's PITA to pull it out of the lists of some shitheads, like SpamHaus.

Source: guess it

charles_f|2 years ago

Side note - the privacy consent is downright aggressive. If you want to remove your consent you have to unselect 100+ checkboxes for each of the partners, whereas accepting is a simple "accept all". I bypassed using reading mode, but darn...

throwawaaarrgh|2 years ago

> Maybe the fake contact information of my Microsoft Account make them worry that I am not a good guy.

beretguy|2 years ago

What if I don’t have a blog?

issafram|2 years ago

TL;DR emailed Microsoft a few times

freetanga|2 years ago

I think that governments should offer one free email account per citizen for life. Which you could use or not, but is there for you as a digital inbox… which are the options?

- Self hosting is a bit elitist - not for the masses.

- A paid-for option (proton, tutta,…) would be cataloged as elitist. People perceive email as free.

- A free option provided by a Corporate player will gravitate towards monopolies and lack of privacy.

- A free for life government issued, easy to recover digital point of contact where all your government interactions are pointed towards would be a great step. You could still have a separate one if you don’t trust big brother, but at least your “recovery” address would be secure for life.

tambre|2 years ago

Estonia has personalidentificationcode@eesti.ee and registrycode@eesti.ee, which you are supposed to set up to forward to your actual email aadress. Unfortunately these are restricted for use by governmental agencies for important official notifications (e.g. you're being conscripted, your marital status changed, something has changed in regard to a property you own). [0]

You could create a public alias of the form firstname.lastname.n@eesti.ee, but creation of those was ended in 2018 and they were shutdown in November 2023. [1]

[0] https://www.eesti.ee/en/using-the-state-portal/terms-of-noti... [1] https://www.eesti.ee/en/closing-alias/closing-alias

cogman10|2 years ago

Remember when the US gov did that with a number? The SSN?

I don't know how you can make something like this "easy to recover" without introducing giant security problems.

blcknight|2 years ago

This would probably work in a lot of European countries or places with high levels of government trust. I could see the German post office for example offering something like this and getting wide acceptance.

You’ll have a lot of distrustful Americans commenting how terrible this idea is and the government can’t be trusted. They’d rather get it from a corporation and be subjected to unlimited surveillance capitalism and manipulation.

YetAnotherNick|2 years ago

I really don't understand how people think government issues services have more privacy, when in reality it is the exact opposite. It didn't even take NSA leaks to know that government privacy violations are lot more both in terms of quantity and the impact. I would never use a government email if it is tied my real self.

At least in my country I know for a fact that data which should be legally private is used by political party plans and by the police.

b112|2 years ago

A paid-for option (proton, tutta,…) would be cataloged as elitist. People perceive email as free.

The era of Pii as a commodity is coming to a close. The writing is on the wall for this.

Once that happens, free email will vanish. Poof. Gone. So will many other "free" online things.

This period of most people getting free email is really quite short historically. A decade.

(Many people used to get email addresses from their ISP, which were part of their paid plan)

I wonder what will happen when gmail goes paid. It's going to happen, and I expect so regionally (eg, not the EU zone or some such) within 5 years.

A lot of people depend upon said free email, and as much as I dislike Google, they have absolutely zero obligation to give anything away.

They've spent the last few years moving classes of accounts to paid. They've been closing down accounts which seem dormant.

Soon... a year maybe?, I think we'll see some sort of precursor change. A reduction of storage for free accounts, or number of emails you can send, or something.

chris-orgmenta|2 years ago

> - Self hosting is a bit elitist - not for the masses.

Is it? Most people, including nomads & unhoused, seem to have smartphones these days (at risk of theft, but arguably easily replaceable). And 4/5G/PublicWifi connectivity in urban areas is so saturated.

I wonder, is it reasonable for me to want government investment and legislation (but no other state interference) into some open source server project that we can run on our phones for this? (heck, give us mesh network functionality too while you're at it).

And am I reasonable in my (left-leaning thought) that, like sexual health consumables, mobile phones should be subsidised by tax revenue, along with other necessities/'empowering tools'?

fauigerzigerk|2 years ago

I think there are more effective ways for governments to intervene. There are essentially two separate issues:

1) Permanent allocation of names and numbers

2) Interoperability standards and rights allowing us to link names and numbers to service contracts.

Once these issues are regulated in a consumer/citizen friendly way (like they did with phone numbers in the UK), governments could provide some sort of default service on top of it, but in my view this is not the most important part.

rafaelrc|2 years ago

> A free option provided by a Corporate player will gravitate towards monopolies and lack of privacy.

Just like a "free" government option?

PedroBatista|2 years ago

Some have an obligatory and officially free email account for you... to receive notifications.. to pay taxes.

judge2020|2 years ago

You'd still need to be able to block these addresses or at least have a reputation system for them, otherwise telemarketers would just tank their own reputation for some sales, or people would pay the homeless to sign up and let them send spam via their digital inbox.

Almondsetat|2 years ago

I agree. You shoukd have unlimited inbound and limited outbound emails between citizen accounts and a 10 email limit for outside addresses.

This way you can sign up to a third party email service and use your permanent and guaranteed government one as a recovery address

regularfry|2 years ago

In practical terms the government-issued option would be provided by a corporate player. Option 4 is option 3.

briandear|2 years ago

I definitely don’t like government being involved with that. Because it would evolve into “you must use your official government provided email address for <whatever>.” And once that address gets out there, you’ll be spammed your entire life because companies and governments and credit bureaus and other potentially annoying actors would know that’s “your” email address. Hard pass.

mulmen|2 years ago

The United States already has that. It’s called the United States Postal Service.

benbristow|2 years ago

Ah yes, a government owned email service, what could go wrong?

ekianjo|2 years ago

Government is the entity I trust the least with my communication. No thanks.

j-bos|2 years ago

I mean, iirc in the USA the postal service is a consitutionally mandated service. So this could be (legally) done "overnight" simply by defining electronic mail sevice as a form of postal service. Plus that would be an email service subject to the privacy protections of the USPS.

ostensible|2 years ago

Why not avoid fighting these windmills by using any of the existing commercial mail relays for sending — like SES or mailchimp?

dclaw|2 years ago

We shouldn't have to. These companies are fucking ridiculous and blanket ban entire swaths of the internet from sending email.