Yesterday, Microsoft Teams—a combination instant messaging, chat, and collaboration package competing with Slack and the new version of Google Hangouts—was inaccessible for several hours, from approximately 8:30am to 11:30am ET.
By 10:30am, Microsoft acknowledged on Twitter that the outage was the result of an expired SSL certificate. Approximately an hour later, they had secured a replacement certificate and began deploying it in production, with service widely restored by Monday afternoon.
This isn’t Microsoft’s first major public embarrassment due to a service renewal failure. The company was responsible for one of the most famous “oops, we accidentally the whole domain” incidents in 1999, when it allowed the domain registry for passport.com to expire. The domain was responsible for authentication for a variety of Microsoft services, including Hotmail.com and Microsoft Messenger.
Shortly after Passport.com’s expiration made the front page at Slashdot, a Hotmail user who says he “wanted to see what would happen” paid the $35 renewal fee himself, restoring service. Microsoft later reimbursed the good Samaritan, Linux consultant Michael Chaney, with a $500 check that he in turn auctioned off on eBay for $7,100, donating the proceeds to charity.
A few years later, Microsoft dropped the ball on domain registration again, allowing hotmail.co.uk to go dark in 2003—and this time, the private individual didn’t just pay the fee, they actually bought the domain. Happily, the anonymous individual who purchased the expired domain did not change its DNS records and transferred it back to Microsoft shortly afterward.
The company has not yet made a postmortem analysis of yesterday’s Teams failure available. Most reports have characterized it as somebody forgetting to renew the certificate, but it’s equally possible that an automated renewal system failed and no one at the company detected the problem until after the service was widely reported as down.
We won’t presume to tell Microsoft how to run a 20 million user service, but smaller operations can easily avoid similar issues—the EFF’s Certbot automates renewal of free Let’s Encrypt SSL certificates, and the Nagios monitoring system includes a plugin that automatically tests deployed SSL certificates and warns its operator if they are approaching their expiration date.
Google has announced that end-to-end encryption is rolling out to users of Google Messages, Android’s default SMS and RCS app. The feature has been in testing for months, and now it’s coming to everyone.
Encryption in Google Messages works only if both users are on the service. Both users must also be in a 1:1 chat (no group chats allowed), and they both must have RCS turned on. RCS was supposed to be a replacement for SMS—an on-by-default, carrier-driven text messaging standard. RCS was cooked up in 2008, and it adds 2008-level features to carrier messaging, like user presence, typing status, read receipts, and location sharing.
Text messaging used to be a cash cow for carriers, but with the advent of unlimited texting and the commoditization of carrier messaging, there’s no clear revenue motivation for carriers to release RCS. The result is that the RCS rollout has amounted to nothing but false promises and delays. The carriers nixed a joint venture called the “Cross-Carrier Messaging Initiative” in April, pretty much killing any hopes that RCS will ever hit SMS-like ubiquity. Apple executives have also indicated internally that they view easy messaging with Android as a threat to iOS ecosystem lock-in, so it would take a significant change of heart for Apple to support RCS.
The result is that Google is the biggest player that cares about RCS, and in 2019, the company started pushing its own carrier-independent RCS system. Users can dig into the Google Messages app settings and turn on “Chat features,” which refers to Google’s version of RCS. It works if both users have turned on the checkbox, but again, the original goal of a ubiquitous SMS replacement seems to have been lost. This makes Google RCS a bit like any other over-the-top messaging service—but tied to the slow and out-of-date RCS protocol. For instance, end-to-end encryption isn’t part of the RCS spec. Since it’s something Google is adding on top of RCS and it’s done in software, both users need to be on Google Messages. Other clients aren’t supported.
Google released a whitepaper detailing the feature’s implementation, and there aren’t too many surprises. The company uses the Signal protocol for encryption, just like Signal, Whatsapp, and Facebook Messenger. The Google Messages web app works fine since it still relies on an (encrypted) local connection to your phone to send messages. Encrypted messages on Wear OS are not supported yet but will be at some point (hopefully in time for that big revamp). Even though the message text is encrypted, third parties can still see metadata like sent and received phone numbers, timestamps, and approximate message sizes.
If you and your messaging partner have all the settings right, you’ll see lock icons next to the send button and the “message sent” status.
As previously announced in April, Apple has today launched its new Podcasts Subscriptions feature on iOS, iPadOS, and macOS. The system allows users to subscribe to podcasts (or groups of podcasts called Channels) for extra perks.
Perks can include early access to episodes, as well as ad-free listening. Some shows may offer bonus content for subscribers as well. You can subscribe to a podcast with just one button using Apple’s payment system.
Podcast creators can charge whatever they please, with the minimum subscription fee being $0.49 per month. Apple takes 30 percent of that amount for the first year, but if a subscriber remains active beyond 12 months, Apple switches to taking just 15 percent of that subscription fee.
Fortunately, Apple doesn’t have any rules against additional ways to monetize podcasts that offer these subscriptions, such as asking listeners to also back a Patreon.
When you subscribe to a podcast, its show page will have a “Subscriber Edition” label on it. You can also trial subscriptions to participating podcasts to see if they’re worth actually paying for. The length of time these trial subscriptions last varies, but it seems to usually be a few days or as long as a week.
Channels are basically podcast bundles curated by someone. Channels aren’t limited to podcasts using Apple’s new subscriptions offerings, though. When you follow more than one channel, a new “My Channels” section will appear in the Listen Now tab of the Podcasts app. Initiating a paid subscription to a channel gives you subscriber status with all its member podcasts.
Podcasts Subscriptions will be available in 170 countries and regions on devices running iOS 14.6, iPadOS 14.6, and macOS 11.4 or later.
A new Windows visual refresh, code-named Sun Valley. is on the way this summer. Until recently, we’ve assumed that this update would simply bring a new look for Windows 10 21H2—the major release of Windows 10 in the second half of 2021—but new information in the form of posted end-of-life (EOL) dates for Windows 10 and a leaked screenshot of something purporting to be “Windows 11 Pro” heavily imply that serious changes are on the way.
Windows 10 EOL in 2025
Rumors of Sun Valley being “Windows 11” have been circulating for months—but until recently, we didn’t put much stock in them. Windows 10 was intended to be Windows as a Service—a radical departure from the prior era of new, major Windows releases every three years or so. It seemed likely that Sun Valley’s “sweeping visual rejuvenation” would result in Windows 10 21H2 looking very different from Windows 10 21H1. Why fix what’s not broken?
The first strong indication that bigger things may be coming landed last week from a Microsoft-published EOL notice for Windows 10. “Windows 10 Home and Pro”—no codenames, no minor version numbers—is now listed as retiring on October 14, 2025. “Retiring” is a part of the Modern Lifecycle Policy and means that the retired product leaves support entirely; this does not follow the old Fixed Lifecycle Policy with “mainstream” and “extended” support. Retired is retired—hit the pasture.
As Windows Central points out, the retirement date isn’t entirely a new phenomenon—Microsoft initially launched the operating system with “mainstream support” through October 2020 and “extended support” through October 2025, the same five-/10-year-support period it provides for server and enterprise operating systems. What has changed is the way Microsoft talks about that end of support—there was no retirement date for Windows 10 as a whole shown on the home-and-pro life cycle page until recently.
There isn’t any real question about the end of life at this point—Microsoft has published it, and we have no reason to think it won’t happen. The interesting questions revolve around what comes next and when it will happen.
Windows 11 in 2021?
We’ve been seeing rumors about Sun Valley being a new Windows 11 for a few months—and until Microsoft posted a fresh EOL for Windows 10, we were skeptical. Windows 10 has been touted as “Windows as a Service” with no real expiration date for some time now, and there was no real reason to expect anything different.
The end-of-life date for Windows 10 as an entire operating system changes that—and it’s backed up by leaked screenshots of a Windows build claiming to be “Windows 11 Pro” which showed up today on Baidu. The new build is visually similar to the canceled Windows 10X, and its screenshots appear legitimate. (The Verge says it can “confirm they are genuine,” with no details as to how.)
What does a new version of Windows mean for me?
For now, it’s unclear what a new “Windows 11” means for end users—there are no guarantees that existing Windows 10 licenses will allow the use of Windows 11, let alone an in-place upgrade. We also have no concrete idea about when new releases of Windows 10 will cease, when the first Windows 11 will be available, or what costs will be.
We do have an educated guess or two, though—Microsoft’s generous upgrade policies from Windows 7 to Windows 10 (you can still upgrade for free today!) strongly imply a similar policy for 11, which Microsoft will presumably be keen to get users on. We also don’t expect under-the-hood changes as sweeping as the ones which took place between 7 and 10. In all likelihood, in-place upgrades will be available.
We’d also like to point out that the consumer support cycle for Windows 10 is short. For example, Windows 10 21H1—the most current build—is only supported through December 2022. That’s a roughly 18-month lifecycle, and there are no extended support policies for consumer Windows anymore. When it leaves support, you’re expected to upgrade to the next version if you want to continue getting support and bugfixes.
We may or may not see a Windows 10 21H2 or even a Windows 10 22H1. But we don’t expect to see a new Windows 10 build past 2023 at the latest since that would imply the need to support 10 past its October 2025 retirement date.
More details are on the way
If you find the lack of concrete detail here frustrating, you’re not alone. Fortunately, the wait won’t be long—Microsoft’s What’s Next for Windows digital event is coming June 24, and we expect plenty of screenshots, news, and more detailed upgrade guidance at that time.