iMessage NOT syncing across iPhone and MacBook Air AGAIN

Hey chaver,

We'd be happy to help out. From your post it's not clear whether the messages not syncing are SMS or iMessages. If they are SMS though, you might have an issue with text message forwarding between your iPhone and your Mac. To fix this, be sure this is enabled under Settings > Messages > Text Message Forwarding and enable it for your Mac. This is outlined further here: Forward SMS/MMS text messages from your iPhone to your Mac or iPad - Apple Support

If these are iMessages, make sure Messages in iCloud is enabled on both devices correctly:

Set up iCloud for Messages on your iPhone, iPad, or iPod touch

1. On your iPhone, iPad, or iPod touch, go to Settings > [your name] > iCloud.

2. Do one of the following:

• iOS 16, iPadOS 16, or later: Tap Show All, tap Messages, then turn on Sync this [device].

• iOS 15, iPadOS 15, or earlier: Turn on Messages.

Any messages currently stored in iCloud are now accessible on your device, and any new messages you receive on your device will be stored in iCloud.

3. To make sure you can see your messages on all your devices, also check the following:

• iMessage account: On your iPhone, iPad, or iPod touch, go to Settings > Messages > Send & Receive. Make sure that you’re signed in to iMessage with the same Apple ID. You can choose which email addresses and phone numbers you want to send and receive messages from on each device.

• Text message forwarding: If you want to receive SMS and MMS messages on all your devices, go to Settings > Messages > Text Message Forwarding on your iPhone. Turn on text message forwarding for each device. For more information, see the Apple Support article How to forward SMS/MMS text messages from your iPhone to your iPad, iPod touch or Mac.

4. To see messages stored in iCloud, open the Messages app.

For more information on how to use Messages on your iPhone, iPad, or iPod touch, see any of the following:

• iPhone User Guide: Send and receive messages on iPhone and Collaborate on projects with Messages on iPhone

• iPad User Guide: Send and receive messages on iPad and Collaborate on projects with Messages on iPad

• iPod touch User Guide (iOS 15 or earlier): Send and receive text messages on iPod touch

Set up iCloud for Messages on your Mac

1. In the Messages app on your Mac, do one of the following:

• macOS Ventura: Choose Messages > Settings, click iMessage, then select Enable Messages in iCloud.

• macOS 12 or earlier: Choose Messages > Preferences, click iMessage, then select Enable Messages in iCloud.

2. Select which email addresses and phone numbers you want to send and receive messages from on your Mac.

Any messages currently stored in iCloud are now accessible on your Mac, and any new messages you receive on your Mac will be stored in iCloud.

Note: If you want to see SMS and MMS messages on your Mac, see the Apple Support article How to forward SMS/MMS text messages from your iPhone to your iPad, iPod touch or Mac.

3. To see Messages stored in iCloud, open the Messages app.

Note: If you want to turn off Messages in iCloud on your Mac, deselect Enable Messages in iCloud. You can choose to disable Messages in iCloud for all your devices, or just your Mac.

For more information on how to use Messages on your Mac, see the Send a message on Mac.

This is outlined further here: Set up iCloud for Messages on all your devices - Apple Support

We hope this helps out. If you continue to have issues though, contact Apple here: Get Support

Take care!

Hi chaver,

Since you mentioned that two of the contacts available on your iPhone aren’t syncing to your Mac as well, try the steps in this article to get them syncing again: If your iCloud Contacts, Calendars, or Reminders won’t sync - Apple Support If they sync with your Mac, see if one of them can send you a message.

You mentioned your Mac recently being updated, is your iPhone also up to date? The latest available is iOS 16.2. You can confirm what version is currently installed on your iPhone by going to Settings > General > About.

If an update is needed, you can do the following:

1. Back up your device using iCloud or your computer.
2. Plug your device into power and connect to the internet with Wi-Fi.
3. Go to Settings > General, then tap Software Update.
4. Tap Install Now. 
5. 
   

Update your iPhone or iPad - Apple Support

Take Care!

Hello chaver,

Thanks for updating us with this information and clarifying that for us. We understand you've taken some great steps already to try to clear this up, but let's check Text Message Forwarding once more on your iPhone and MacBook Air. We'll include the steps below to check this quickly, and you can find more details here: Set up iPhone to get SMS messages on Mac - Apple Support

1. On your iPhone, go to Settings > Messages.

2. Tap Text Message Forwarding.

Note: If you don’t see Text Message Forwarding, make sure you’re signed in to iMessage using the same Apple ID on both your iPhone and your Mac.

3. Turn on your Mac in the list of devices.

4. If you’re not using two-factor authentication, a six-digit activation code appears on your Mac; enter this code on your iPhone, then tap Allow.

If you're still unable to receive the forwarded message, confirm with the provider if this may be blocked on their end. If this isn't affected by your provider, contact Apple Support directly to check into this with you in more detail.

Have a great day!