Given the age of the tags and the symptoms you’re describing, this is almost certainly battery compatibility or contact-related, not an iOS or phone issue—even though the timing makes it feel like software.
Here’s what I suggest you try next, in order, before your Monday trip:
- Double-check the exact battery model. Even though the AirTags beep, many CR2032 batteries sold today have a bitter coating that prevents proper electrical contact.
- Use a non-coated CR2032 (Duracell non-bitter, Energizer, or Panasonic)
- If unsure, lightly wipe the battery with isopropyl alcohol and a lint-free cloth
- Make sure the positive (+) side is facing up. I know, I know, but anything is possible.
- Stretch the battery contacts (very gently). After ~2 years, the spring contacts inside AirTags can relax just enough to cause intermittent power. If the contact isn’t perfect, the AirTag will beep but won’t complete pairing.
- Remove the battery
- Use a plastic tool or fingernail to slightly lift the metal tabs inside the AirTag
- Reinsert battery and close firmly (you should feel a solid click)
- Force a full reset (even if you’ve tried before). Again the 5th beep should sound different from the first four. If you never get the different tone, that’s a strong indicator of hardware or battery incompatibility.
- Remove the tag from your Apple Account. Open Find My → Items, and if the AirTag appears even as offline:
- Remove it completely from your account
- Restart your iPhone
- Bring the AirTag next to the phone and re-pair
- Double-check your iPhone settings:
- Bluetooth ON (toggle off/on)
- Location Services → Find My → Precise Location ON
- Apple Account signed in correctly
- No VPN enabled during pairing
Finally, two-year-old AirTags that suddenly refuse to re-pair after a battery change—especially when they beep but won’t reset—are often end-of-life units. Apple doesn’t advertise this, but internal failures do happen.
At this point, with travel days away, I’d strongly suggest buying a new AirTag (or two) as backup insurance. If you have time, Apple may replace them if diagnosed faulty—but that’s unlikely before Monday.