Solution to a “Jeopardy!” streaming conundrum: What is Tailscale?
It is perhaps not surprising that my spouse and I raised a Jeopardy! fan. Our older child, halfway through college, not only loves the show but has developed an encyclopedic knowledge of geography, transit systems, musical instruments, and much more. Or should I write encyclopaedic, as they are spending this current term in London on a study abroad program? That plays into the story.
If you have followed my career, you will know both that I won two episodes of Jeopardy! (just like Dan Moren) and that I have a nearly obsessive interest in ways to enable remote access to and control of your Mac and other devices when you are outside your local network. I have, in the past, even written an entire ebook on the topic.
London, Jeopardy!, and remote access and control all intersect when I received a text from said child late in the evening, their time. The system we use (and updated) is a good solution for any locally recorded or stored media files.
Who is Rube Goldberg? We would also have accepted Heath Robinson
It surprises people who haven’t watched Jeopardy! for years that it was not available on a streaming platform, only over-the-air (OTA).1 This was for a funky reason: it’s a syndicated program, just like a lot of talk shows and game shows have been. They don’t make their money selling the rights to air the program, like production companies and studios do with broadcast or streaming services. Rather, the shows bring in the big bucks through a combination of local and national advertising, a decent portion of which flows back to the syndicated programs’ creators.2
Once a show aired, that was it—unless you caught it as a re-run, recorded it to a DVR, or found a pirated version online, you could never watch it again. Jeopardy! was ephemeral in its nature, anyway, except if you appeared on it. (Yes, I still have my DVR-recorded digital files of my appearances!)
I say was because, as of the week of September 8, you can watch Jeopardy! on Peacock, Hulu, and the horrible set of words “Hulu on Disney+” the day after the episodes air in syndication. It took until 2025 for the money from next-day streaming—carved out years ago—to be good enough to risk annoying stations syndicating the program.3
However, I set up an OTA DVR system many years ago that still does the trick—and lets me skip commercials. I record Jeopardy! as follows:
- An antenna mounted on our roof
- An HDHomeRun TV tuner, a networked TV tuner, plugged into that antenna
- Channels DVR Server, a software DVR that is compatible with HDHomeRun and other products, and also allows remote access
As a result, I have HD-quality recordings of Jeopardy! that we can watch at our leisure. And when our older returned to college last year, I figured out a missing piece in our setup that let them watch from Boston.
What is “Back to Back to My Mac”?
When Apple released Back to My Mac in 2007, I was overjoyed. When I traveled for conferences, I carried a laptop—but remember the low-capacity hard drives we had in those days. I regularly would need a file I hadn’t brought, or even need to use an app on my machine, back at my office.4
There were third-party offerings, like Timbutku Pro, but they were designed for corporate environments. They didn’t cut through what had quickly become the typical configuration for home Internet service providers (ISPs): using NAT. Network Address Translation allowed a gateway (often a Wi-Fi router or broadband modem) to create a local area network (LAN) using addresses drawn from a private pool. These private addresses were reserved from the public Internet and could not be routed. As such, they could be reused.
A gateway uses a public IP address on the Internet (wide area network or WAN) side, either as a broadband modem or assigned by that modem. The gateway employs DHCP (Dynamic Host Configuration Protocol) to assign private addresses on the local network. Devices on the LAN talk to each other using their private addresses. When they need to reach out to the Internet, the NAT software creates a mapping of their private address to the public one, allowing traffic to flow.
But what about traffic inward, such as running a server or, say, accessing a Mac’s screen remotely? That requires setting up fixed pairings of ports—essentially a sub-address on an IP address—to the public IP address and a private one. This punch-through setup varies for every router, and, in the past, often didn’t work at all—or at least not reliably. It’s a little better in recent years.
Some people were further bedeviled by a “double NAT.” This nesting problem happens when your ISP doesn’t let you install your own gateway. So the broadband modem hands a private address to the gateway you’re using, which, using its own NAT software, creates a nested, distinct private network for your devices. This works fine for outbound traffic, but usually fails without a lot of effort for inbound.
Back to My Mac mostly worked—double NAT could defeat it, but not always. It wasn’t perfectly reliable, as the service would sometimes die on a Mac for whatever reason and not revive itself, a sticky problem when you couldn’t restart it because…you needed remote access to do such a thing.5
With Back to My Mac enabled and working, you could effectively have a tunnel back to your office, with shared volumes on the Mac and its screen available for connection. Apple discontinued Back to My Mac in 2019. However, by that time, a number of companies had developed robust screen-sharing and remote-volume-access packages, such as Screens and Splashtop. These require installing client software, and have a range of prices from “free with limits” to “only a corporate IT person needs this set of features at this expensive per-seat price.”6
These tools don’t fit every need, however. For what you generally need, you have to pay a fee that’s about $25 to $60 per year for a single user or a couple of devices. And you are subject to the limitations and choices of the company’s tools.
What if you could have broader network and service access to your local machines, pay as little as nothing in many cases, and use whatever software you wanted? This is where my favorite product of 2024 kicks in: Tailscale.
Who is a surprisingly successful Canadian company?
Tailscale has a very straightforward offering: an extension of a virtual private network (VPN), which securely tunnels traffic between two points.7 You use a VPN to protect your data from ne’er-do-wells sniffing for open traffic at a coffee shop or on unprotected networks.8. A VPN service creates an encrypted tunnel between your device and a data center, obviating most interlopers; corporate VPNs go from your device to inside the corporate network.
Tailscale uses VPN technology, but instead of popping you out elsewhere on the Internet, it essentially creates a VPN LAN—a central, routable, networked space that all your devices connect to. This pool is reachable from the public Internet, so you can connect when your devices are out and about without any calisthenics. Tailscale built its system with end-to-end encryption, so only the endpoint VPN clients—not the company—have access to the encryption secrets used to secure sessions.
Any resource you could access while on the same network as your devices can be reached via the Tailscale connection. The company has done a lot of clever work to bypass NAT limitations, too, so even the most bizarre configuration won’t defeat two-way connections. The only real limitation is that Bonjour traffic doesn’t pass over Tailscale for quite technical reasons. (Bonjour is a multicast, broadcast protocol that doesn’t work within the parameters of the Tailscale approach.)
Because of the lack of Bonjour, you have to do a slight amount of work to find the addresses assigned by Tailscale to the machines connected to your pool. The Tailscale software on each connected device lets you see the IP address and name of that device, plus all the other connected devices’ names. If you want to connect to a Mac with file-sharing enabled, you just choose Go > Connect to Server in the Finder and paste that IP address in; the same works with screen sharing in the Screen Sharing app. (I wrote a much more detailed look at Tailscale over at TidBITS last year, with step-by-step setup instructions. Folks in the comments offered some great insight about further uses and configurations.)
“Hey, Glenn, you promised this would explain setting up remote streaming for Jeopardy! Get to the point!”
Ok, ok! So Tailscale offers both clients for end users and API-based integration. The people who make Channels built a Tailscale client into their Channels DVR server. Once I had an account set up, I turned on the Tailscale client within Channels DVR and approved the connection at the Tailscale administrative console. I sent an invitation via Tailscale to my kid, who installed the Tailscale client on their laptop, and I approved them as part of my group. They could then use a browser to connect to the home DVR server and stream their favorite trivia program at will.
The problem that got us on the phone a few days ago, however, was that the intervening network steps seemed to be slowing streaming to a crawl—under 1 Mbps, despite their dorm network showing nearly 70 Mbps downstream. Channels doesn’t allow downloads of programs via the browser, so we set up an additional connection through their iPhone, went through the approvals for that, and they were able to plug in the Tailscale IP address for the Channels DVR server, make a connection, and download the show, which they can AirPlay from their phone to their laptop to watch on the “big” screen.
While this is a specific case, you can use Tailscale more broadly with any home streaming resource, like Plex, files on network-attached storage (NAS) systems, or even Apple’s funky Home Sharing system found in the TV app on a Mac. Any file, screen, or network resource you need becomes fully accessible.
You can also use Tailscale as a VPN to your home network, which can make resources (like country-locked streaming services) available without paying for a separate VPN service. The easiest way is through an Apple TV.
When I was out of the country earlier this year for a few weeks, I was able to use Tailscale to “keep in touch” with material I needed from my home computer, access U.S.-only services, and, yes, stream Jeopardy!
There has to be a catch, right? It’s the price. It’s free! Free if you’re using it for personal use and using a non-corporate email account. The company has a simple definition of what personal means: “In this scenario, your Tailscale account is owned by you solely for your own personal use.” Free accounts can have up to three users and 100 devices.
If you need a greater range of personal access or four or five users, a $5 per month Personal Plus package provides that. For commercial uses, most of us almost certainly don’t need more than the $6 per user per month Starter offering.
And, now, back to our program. Ken, I’ll take Nattering Network Nonsense for $600, please.
[Got a question for the column? You can email glenn@sixcolors.com or use /glenn in our subscriber-only Discord community.]
- A limited number of back episodes were available for a while on some streaming services. ↩
- In fact, Jeopardy!‘s producing company, Sony Pictures Television, sued its national advertising partner, CBS, over advertising revenue just last year. ↩
- In 2028, when current licensing deals end, Sony could opt to stream same day. ↩
- For about 15 years, I shared offices with other freelancers, and had a desktop Mac in my office with lots of hard drives attached that I would also want to access from home when I wasn’t at work. ↩
- At one point, many of us running servers remotely had the most ridiculous thing. The Sophisticated Circuits’ PowerKey Pro was a power strip that you could plug into a phone line, such as one you already used for a fax machine. (I’m not going to explain a fax machine.) It could listen to Touch-tones (not going to explain that, either) that it interpreted as commands, including to cycle power on a given outlet. ↩
- TeamViewer charges high fees compared to other companies to use its commercial version, but offers a non-commercial option for personal use. However, the company decides in an unknown fashion what it considers “commercial” use and starts displaying warnings and cuts you off when it decides you’ve used it that way. I don’t like it. ↩
- One of the most successful and fastest-growing tech companies in Canada. ↩
- Nearly all network traffic to and from your devices is secured via encrypted tunnels, and some uses end-to-end encryption, like iMessage. However, the domain names of sites you visit and other data can leak, and there remain some apps and Web sites that stubbornly avoid encryption, for whatever reason. ↩
[Glenn Fleishman is a printing and comics historian, Jeopardy champion, and serial Kickstarterer. His latest books are Six Centuries of Type & Printing (Aperiodical LLC) and How Comics Are Made (Andrews McMeel Publishing).]
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