Apple Watch 1st Gen

Hey AdamMc1,

Thanks for asking Apple Support Communities about the issue you're having with pairing your Apple Watch with your iPhone. You should be able to pair those together. You'll want to first back up your iPhone, then update to the current software version of 14.1, as an update was recently released. Then, restart your iPhone as well as your Apple Watch and try to pair it again. Here are some great guides to follow, just in case:

How to back up your iPhone, iPad, and iPod touch

Update your iPhone, iPad, or iPod touch

Update apps or use automatic downloads

Then, try to pair your watch again: Set up and pair your Apple Watch with iPhone

If you're still having trouble after those steps, you'll want to reach out to Apple Support directly. They can be reached here: Get Support

Thanks again, and have a wonderful day!

This is a known problem with ios13 and now ios14,they don't seem to like older watches with watchos5 or below,here are some proven solutions from other forum

members.

Quote;

Apple watch 2;

I found a friend, who was on iOS 12 and used his iPhone to pair. Before

pairing it asked to upgrade the watch OS (iOS 13 didn't offer this option).

After I upgraded the watchos I unpaired the watch from the ios12 phone and

then was able to pair it with any iPhone running iOS 13.

Quote;

1st gen apple watch;

pairing was successful on the following device (with associated OS)

to pair via bluetooth I used an iphone 7 with iOS 12, after pairing

immediately accepted the watchOS update to version 4.3.2 after everything

was successfully equipped with the last update, unpaired the iPhone and the

Apple Watch a reset (factory settings) all this took some time but afterwards

pairing on an iPhone XR with iOS13 g was a piece of cake.

Quote;

May 9, 2020 4:58 AM in response to Hashimsabbah

Just did this with a series1. I had to pair with the original phone and update

the firmware for me to pair correctly. All I did was ask to pair and the update

happened on an iPhone 6.

Quote;

nickfit888

Jul 5, 2020 5:23 AM in response to fieryjack

So the “pairing with an old iPhone on iOS 12” trick actually worked for me. I

got a brand new series 3 Apple Watch via a warranty replacement from

Apple. I could not pair the watch to my iPhone X due to the 5.3.7 update

issue. Originally it allowed me to update to 5.3.7 but it was stuck after that.

Based on the advice from “fieryjack” I took an old iPhone 6 (iOS 12.4.7) and

was able to pair my Apple Watch. Once it was paired (watch was fully set

up and synced to the iPhone 6) I tried to update the Watch OS but it said I

needed up update the iOS in order to do so. I unpaired the watch from the

iPhone 6 and paired it with my iPhone X (running iOS 13.5.1). Not sure if

this additional step helped but I chose the manual pair option and this time

the watch gave the option to update to 6.2.6! Once it started updating i

turned off the Bluetooth on my iPhone so that it would update faster using

the wifi network (assuming you are connected to a fast wifi network). I

think it took between 2-3 hours to download the update and after that i was

able to restore my watch using a previous back up.

Thanks again fieryjack for the tip!

Find a phone with ios12 on it if you can and pair your watch to it,it will ask

you to update the watch select yes,after it has updated unpair the watch

from the ios12 phone and then pair it with your ios13 or 14 phone.Now you can update to watchos6 and or above.

Alternatively contact apple store and see if they will update the watch

through the watch's data/diagnostic port.