Fresh Tech Questions From Readers, Solved
Wow – you all keep the questions coming faster than I can answer them on the radio!
I’m still reading every single email myself (yes, really) and replying when I can.
If I don’t get back to you personally, there’s a good chance your question ended up in this newsletter or on the Feedbag segment.
Thank you for trusting me with your tech headaches – I love solving them.
Here’s the latest batch of Dear Rich. Keep them coming!
Apple Watch won’t pair with new iPhone
Ellison in Los Angeles writes…
Hi Rich, love the show. My Apple Watch is about two years old and it still tries to connect to my old iPhone. I just got a new iPhone and it won’t pair – it doesn’t even show up in Bluetooth. Any advice?
Ellison, this is super common. Your Watch is still “married” to the old phone. The fix is simple:
If you still have the old iPhone → open the Watch app and unpair the watch from there (it will make a backup).
If you already got rid of the old phone → on the Watch itself go to Settings → General → Reset → Erase All Content and Settings.
After that, it will act like a brand-new watch and show up ready to pair with your new iPhone.
Preserving handwritten recipes with AI
Bob in Charlotte, NC writes…
I have dozens of handwritten recipe cards from my mom (1950s–70s). You recently talked about using AI to clean them up. Do I need a scanner?
Bob, no scanner required! Just lay each card on a table, take a well-lit photo with your phone, and drop the picture into ChatGPT or Google Gemini.
Tell it: “Transcribe this handwritten recipe into clean typed text with ingredients and instructions.” It does a really good job, even with old cursive.
Save each one into Apple Notes, Google Keep, or your notes app of choice and you’ll have a searchable family cookbook in no time.
Shrinking PDFs, photos, and videos for email
Steve in Vancouver, WA writes…
My scanned PDFs are 2–3 MB each, photos the same, videos are huge. I miss the old Picasa compressor. What free tools work great today?
Here’s my current go-to free toolkit:
PDFs → Smallpdf.com or CleverPDF.com (drag & drop, no sign-up needed for basic use)
Photos → TinyPNG.com (great quality even after heavy compression)
Videos → HandBrake (free desktop app – drop the bitrate or resolution and turn gigabytes into megabytes)
All three are completely free for normal use and will save you a lot of time and megabytes.
Google Calendar history disappearing
Beverly writes…
Events on my Google Calendar vanish after a few years. Should I go back to paper?
Your history is almost certainly still there! Google Calendar keeps everything forever.
The problem is usually that a third-party phone app only syncs a certain number of events back.
Fix: Open calendar.google.com in any web browser (phone or computer), scroll back month by month, and you’ll see everything going back to day one.
Once you confirm it’s there on the website, you can tweak your phone’s sync settings if you want all the history on mobile too - but you might have to download the official Google Calendar app to get this.
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Shopping extensions on a privacy browser
Terri writes from New Zealand…
I use DuckDuckGo browser for privacy. Can I still add shopping-helper extensions like Honey or Capital One Shopping?
DuckDuckGo doesn’t support extensions at all (by design). Look closely the next time you install an extension - it usually says it can read data on all the websites you visit, aka it’s collecting a lot of info for a “free” tool.
If you want a privacy-first browser that still lets you run all the normal Chrome shopping extensions, you can switch to Brave. It blocks trackers by default and supports the full Chrome Web Store – so you get a good mix of both worlds.
Parking an old landline/business number
Rich in North Tustin, CA writes…
I want to cut my landline but keep the number for occasional use. Google Voice? Something else?
Google Voice probably isn’t your best bet because it’s tough to port landlines to it. They typically only take mobile numbers. So you would have to first port to a mobile carrier, then GV, which is a pain.
A better bet might be to sign up for a super-inexpensive plan from a carrier like Tello that lets you build your own cell phone plan. No data and 100 minutes with free texting would be around $5 a month.
Another option if you don’t want to use the number but keep it is NumberBarn. They specialize in “parking” numbers for $2–5/month. You port the number in once, then you can forward it anywhere, set up voicemail, or just let it sit.
AI translator device worth it?
Tony writes…
I saw an ad for a $79 E****e Translator that claims 68 languages offline. Too good to be true?
I’m skeptical of the super-cheap translators that flood social media with ads.
The trusted brand here is Timekettle. I haven’t personally tested it, but I did submit a request for a sample of their T1 translator so I can get a better idea of how it works.
If you don’t want another gadget, the free ChatGPT and Google Gemini apps already do excellent live voice translation (and keep improving every month). You could also download Google Translate or Apple Translate and save a language for offline translation.
True off-grid GPS in a new car
Tom in La Palma writes…
I want to buy a Toyota but they don’t have built-in GPS. Everything now wants a subscription or my phone. I want real GPS that works with no cell service.
Your phone already has a true GPS receiver that works 100% offline. Before you leave cell range, open Google Maps or Apple Maps and download the offline map for the area.
Your blue dot and turn-by-turn should work perfectly, even in the middle of nowhere.
That’s it for this round! If you’ve got a tech question (big or small), hit submit it here and I’ll do my best to help.
See you on KTLA, KFI, and Instagram @richontech.
Rich
Love the Dear Rich!