This solution worked for me by Ralph Johns from Messages says "Not delivered" on Apple Support Communities. in the "to" spot type in your iPhone Number in full including the country code. This bit will stop any Sync copy showing up from the Send of the Apple ID on the Mac.

How to Resend a Message “Not Delivered” from Mac Messages

How to Resend a Message “Not Delivered” from Mac Messages

A similar trick can be done on the iPhone and iPad when messages fail to send from iOS too, again this is usually the result of inadequate internet data connectivity. Another issue you may encounter is the erroneously appearing repeated “message not sent” errors that may show up on a Mac that hasn’t been used in a while yet shares an Apple ID with another active Mac or iOS devices with many messaging activities ongoing.

red exclamation point but not necessarily a “Not Delivered” message as you would with an iMessage, because SMS lacks the read receipts ability.

Can't Send Messages From Your Mac? Try These Steps.

Can't Send Messages From Your Mac? Try These Steps.

Apple’s myriad devices work together seamlessly — except when they don’t. Wait about 30 seconds, then enter your Apple ID details, and sign in to iMessage again. While you’re at it, make sure that your Apple ID details are the same on your Mac and your iPhone. Does the Apple ID account at the top of the page match what you signed into on your Mac? Check to make sure the contact details in Send & Receive are correct. Apple’s Keychain stores passwords and other vital info on your apps and certain processes.

Press Command + Space to open Spotlight and search for the Keychain Access app. From the menu bar, go to ‘File > Lock Keychain “login.”’.

Wait a couple of minutes, then go to ‘File > Unlock Keychain “login.”’. And here’s one more thing to try before contacting Apple’s tech support: delete some plist files. If you don’t see iChat or Messages plists, change the display to sort by list, then click the “Date Modified” option to sort the plist files by when they change. It should change on the fly and iChat/Messages plists should show up at or near the top of the list. If that doesn’t work, return the plist files to the Preferences folder.

What to do when you find iMessage not working on Mac

What to do when you find iMessage not working on Mac

It's a really secure, useful free service Apple makes available to everyone using its various devices, which also supports regular text messaging as well. In your Mac menu bar, click the Apple logo on the top left corner Select “Restart” Follow any on screen prompts to force close apps. CleanMyMac X has a ton of features that aim to keep your Mac operating its best, but one of its more prominent services is ridding your system of unnecessary files and folders.

Instant Mac cleanup Clear messages cache and other redundant files with CleanMyMac X. If restarting your Mac or clearing chat history doesn’t work, an old fashioned logging out and back in scheme may set you on the right path. Open iMessage on your Mac In the menu bar, select “Messages” From the drop down menu, select “Preferences” In the window that appears, select “iMessage” at the top of the window Toggle the checkbox next to “enable this account” off under your Apple ID Toggle the setting back on Quit the Messages app, then reopen on your Mac.

In your Mac’s menu bar, click the Apple logo on the top left corner Select “Date & Time” Click the lock icon at the bottom of the window and enter your password Under the “Date & Time” heading, make sure “set date and time automatically” option is toggled on Click the lock again to secure your Mac. To double-check this setting worked properly, verify both the date and time are correct before closing the window.

Open Keychain Access on your Mac Enter “iMessage” in the search field on the upper right corner of the window. You can send and receive messages on services like Facebook, Twitter, WhatsApp, Skype, Telegram, Slack, Gmail, and LinkedIn.

You have full customization over notifications, and IM+ allows you to send and receive media like videos and GIFs in each chat. iMessage is core to the Apple ecosystem of platforms like iOS, iPadOS, watchOS, and macOS. It’s the central method for exchanging messages, and has become a rich platform with app plugins and other interesting features not found anywhere else. The solutions mentioned today typically iMessage start to work on Mac when it fails, but you should also consider how often you use Messages.

In addition to IM+, you’ll gain immediate and unlimited access to nearly 200 other incredible native Mac apps, all free for seven days! When your trial period ends, continued access to the full Setapp catalog is only $9.99 per month, so why wait?

If you can't send or receive messages on your iPhone, iPad, or iPod

If you can't send or receive messages on your iPhone, iPad, or iPod

Enter the phone numbers or email addresses of your contacts. If you have other issues with a group message, you might need to delete the conversation and start a new one.

To save an attachment in a message, tap the Download button .

IMessage Not Delivered? 6 Ways to Troubleshoot

IMessage Not Delivered? 6 Ways to Troubleshoot

Few things can be more frustrating than when a message doesn't get stamped with the reassuring "Delivered" label. But you're not helpless — here are the most common ways you can troubleshoot and solve this annoying problem.

If you don’t see the “Not Delivered” error, the recipient’s phone might simply not be receiving messages. In the first case — it simply doesn't say it has been delivered, even after several minutes, keep in mind that the most likely explanation is that the recipient's phone is turned off, in Airplane Mode , or has a poor connection.

iMessage needs access to the internet, either via WiFi or a cellular signal, so if you have no service, a network issue, or are in Airplane Mode, the message can't be sent. Check your WiFi and cell signal to make sure your phone can communicate with the outside world. There might be a glitch with your Messages app or your phone's network connection that turning it off and back on again will solve.

To see if it's disabled on your own phone, start the Settings app and tap Messages, then ensure iMessage is on by swiping the button to the right. Generally, if you see this message when trying to send an iMessage, it means you got the iPhone less than a day ago and all of the phone's services are not yet fully activated.

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