Apple touts the end-to-end encryption and overall privacy of its iMessage service, but Sam Biddle of The Intercept reveals a loophole: when you enter a phone number to start a conversation in Messages, the app contacts Apple’s servers to find out whether to send the message via iMessage or SMS. The problem is that Apple’s servers currently log the contact number, the date and time, and your IP address (which could disclose your general location). Apple has verified that it keeps these logs for 30 days and will give them to law enforcement if compelled by a court order. We hope these revelations will encourage Apple to reassess the privacy implications of this system.

In an initiative to improve the health of its employees and customers, health insurance company Aetna is buying Apple Watches for its nearly 50,000 employees and will be offering subsidized Apple Watches to select large employers and individual customers in the upcoming enrollment period, with the remaining cost to be paid via a monthly payroll deduction. Aetna will be providing iOS apps to simplify and improve the healthcare process through care management and wellness, medication adherence, and health plan information and decision support. In addition, Aetna app users will be able to use Apple’s Wallet app to check their deductibles and pay bills. If implemented well, Aetna’s program could improve healthcare, reduce costs, and enhance the company’s ratings with its millions of members.

The first U.S. presidential debate will air tonight, 26 September 2016 at 9 PM EDT. Ben Lovejoy of 9to5Mac has compiled a partial list of the many apps and Web sites that will let you watch live, for free. In addition, as we reported previously, Sling TV is offering a free preview today, which will carry the debate.

Streaming cable alternative Sling TV is offering a free preview of its Sling Orange service from 8 AM EDT on 26 September 2016 until 2 AM EDT on 27 September 2016. The ostensible reason for the preview is to enable cord-cutters to watch the first U.S. presidential debate and the Atlanta-New Orleans game of Monday Night Football, but you can enjoy full access to the 25+ channels included in the Sling Orange service during that time. Signing up for the free preview requires only a username and password, not payment information. You’ll undoubtedly hear from Sling TV afterward, but you should be able to unsubscribe from promotional mailings at that point. Sling TV offers apps for macOS, iOS, and tvOS.

Russian security company Elcomsoft has discovered a major security flaw in iOS 10: encrypted iTunes backups made with iOS 10 allow password-cracking tools to make 6 million attempts per second, more than 40 times faster than with backups created with iOS 9. Apple has confirmed that the issue is real and plans to fix it in an upcoming security update. In the meantime, because the vulnerability could be exploited only by someone with access to your iTunes backups, Apple recommends a strong login password and using FileVault encryption. (The problem also affects backups made in iTunes for Windows.) iCloud backups are immune to the problem, so if you’re concerned about the security of your iTunes backups, you might consider switching them to iCloud.

Yahoo has announced that information associated with at least 500 million user accounts has been stolen by what the company believes is a state-sponsored actor. If you have a Yahoo account, you should change your password immediately and enable two-step verification. In addition, if you use Yahoo as your primary email provider, you should change the passwords for any online account tied to your Yahoo email address, since the thieves could have used password resets to gain access to those accounts as well. More so than any other recent example, this breach shows the importance of using a password manager like 1Password or LastPass to create and enter a separate strong random password for every site.

Congrats to David Sinclair of Dejal, who is celebrating his Mac development company’s 25th anniversary (check out the photo of his original Mac Plus!). Dejal is perhaps best known for its Simon monitoring tool, but the company also makes the free Time Out break reminder app, along with the Caboodle snippet keeper, and the BlogAssist utility for simplifying the process of making HTML markup. Through the end of the month, Dejal is offering a 50 percent discount on all its products.

Forget macOS, there are a number of Mac users who still haven’t made the leap to Mac OS X. Ars Technica profiles the people who stick to the 16-year-old Mac OS 9 and reveals some fascinating reasons for why they persist with such a hoary operating system. For some, it’s a matter of cost, but for others, the classic Mac OS actually maintains technical advantages. In particular, some audio professionals prefer Mac OS 9 for its low latency, high speed, and bevy of free production software.

Peter Cohen reports that many T-Mobile customers who updated an iPhone 6, iPhone 6 Plus, or iPhone SE to iOS 10 suddenly had trouble getting cell service on their phones. Power cycling the iPhone fixed the problem temporarily, but if you’re suffering from this bug, you can now eliminate the error permanently with a carrier update from T-Mobile. Apply it by going to Settings > General > About.

How many iOS text editors are there? We’re not sure, but the number certainly exceeds 100. We know this because text maven Brett Terpstra has, with the help of a number of contributors, compiled a list of more than a hundred such apps, presented in an extensive dynamic chart that lists several dozen features and characteristics of each app. If you’re looking for an iPhone writing tool that can export PDF, costs less than $3, and supports Markdown, Brett Terpstra’s chart is the place to go.

If you love watching football but hate paying for cable TV, Jared Newman of TechHive has compiled an excellent guide to watching NFL games without a cable or satellite subscription. We have one update: Twitter now has an Apple TV app that you can use to watch Thursday Night Football games for free.