Keep Getting "The Bluetooth connection timed out." Error

ToothFairy isn’t recognizing my devices as easily as before. Beyond that, if I click one of my menu icons to connect to my headphones (Airpods Pro & Bose QC 35 IIs) it just spins.

Eventually, an error dialogue box pops up that says, “Your Mac could not connect to “product ID” (“aa-##-##-aa-##-a#”). The Bluetooth connection timed out.” (screenshot of error at the end).

This has been going on for many weeks, I don’t recall when, exactly.

ToothFairy Error

Could you explain what “recognize” refers to here? What did you expect to happen, and what happened instead?

Please see this page.

Hi, Michael—appreciate the quick response.

By “recognizing” I mean, the devices aren’t auto-paired to Bluetooth like they typically are. I’m not sure if that has to do with ToothFairy or MacOS. Normally, I could click any of my device icons and it connected, but now it gives the aforementioned error, and the only way to connect is to go into my Bluetooth settings and connect.

The Bluetooth always has my Magic Mouse & Keyboard connected with no problems. It is only the three headphone devices I have connected to ToothFairy.

Bluetooth pairing is normally only done once per device-Mac combination. ToothFairy is not involved in the pairing process. It only connects/disconnects devices after they have been paired (e.g. via System Preferences ‣ Bluetooth).

AirPods have auto-pairing in that you can pair with one iOS/Mac and then that will sync via iCloud so that you don’t have to pair the same AirPod with another Mac or iOS device. I don’t think Bose devices can do this.

All of this is to say, I’m not sure exactly what you mean by by “devices aren’t auto-paired.” Could you describe this more specifically?

Is this a separate issue from the auto-pairing problem? Or did you write “paired” when you meant “connected”? Please try the troubleshooting steps that I suggested.

Yes, when I said, “connected”, I meant “paired”. My apologies if I’m mixing these up. I know that makes your responses harder.

I am aware that devices need to be connected through Bluetooth settings, but usually they would stay paired. Just like my Magic Mouse & Keyboard, those stay paired and I never have had to go into Bluetooth settings and re-connect or re-pair. Clicking the ToothFairy menu option icons was how I made it active/inactive. Meaning, My Bose icon is an outlined over-ear headphone, but I would click it and I’d hear a beef for it being connected and made active and the icon would fill in and become white.

Bose allows for connection to two devices, so when I used to click the bose icon from ToothFairy it would pretty immediately pair and become active on my Mac.

Are you saying that now you must click the Pair button in System Preferences ‣ Bluetooth?

I think you still have “pair” and “connect” backwards…

Dang it. You’re right, I have the terms backward again.

Anyways, I removed the pairing, from my iMac & from ToothFairy, for my three headphone devices and restarted my computer. I re-paired each of them and added them back to ToothFairy.

It now seems to be working as it should!

Really appreciate your help and patience, Michael.

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