Solve the “Attachment is Too Long” issue in Messages

Updated November 1st, 2022.

My friend Jeff had an interesting problem: he couldn’t send Voice Memos via Messages to a non-iPhone user. He used to do it all the time, but after updating to iOS 14, he couldn’t. I tried it too and it didn’t work for me either.

Trying to send an attachment in Messages to a non-iPhone user
Trying to send a voice memo in Messages to a non-iPhone user

Every time we tapped the “Send” arrow we’d get an error: “Attachment is Too Long.” Hmm.

Continue reading “Solve the “Attachment is Too Long” issue in Messages”

How to Fix iMessage “Waiting for Activation” on iPhone

Updated October 8th, 2020.

Is your iPhone stuck “Waiting for activation” when you turn on iMessage in the iOS Settings? Have you tried everything suggested in Apple’s Knowledge Base article, but still iMessage says “Waiting for activation”? Have you been turning iMessage off, turning it back on, restarting your iPhone, and waiting 24 hours, and still iMessage is “Waiting for activation”?

If so, you’re not alone! It seems iMessage is waiting for activation on a lot of iPhones: a Google search for “how to activate iMessage” yields 546,000 entries. I haven’t read them all, but as far as I know none of them suggest the method described here.

In my opinion, you’ve come to the right place.


EXECUTIVE SUMMARY: turn iMessage OFF, turn FaceTime OFF, sign OUT of iCloud, turn OFF your iPhone. Now, in this order: turn your iPhone ON, turn iMessage ON (signing in there), turn FaceTime ON (signing in there too), and then– and only then— sign into iCloud. Voilá!

  • In Settings, go to Messages and turn off the switch for iMessage.
  • Also in Settings, go to FaceTime and turn that switch off too.

If you were to follow Apple’s instructions, or any of the other articles about this, you’d next switch iMessage back on, or you’d turn your iPhone off, then back on, and then you’d switch iMessage back on… and then you’d still see “Waiting for activation.” Frustrating.

Here’s the magic.

  • After you’ve turned off iMessage and FaceTime in Settings, go to the very top part of Settings, where you see your name, and Airplane Mode, and WI-Fi, and Bluetooth. Tap on your name, leading to the screen with “Apple ID” at the very top, and “Sign Out” at the very bottom. Signing Out is what you’re going to do.

It would be a great idea to have a good look at the iCloud settings before you sign out. It’s likely that your iPhone will remember those settings but just in case, write them down.

  • Now we’re going to sign OUT of iCloud. You’ll have to put in your Apple ID password to do it. When you sign out, you’ll get a big message about saving a copy of the iCloud data onto your iPhone before signing out. Read it carefully. You DON’T want to save a copy on the iPhone.
No, you don't want to save a copy of the iCloud data onto your iPhone before signing out.
No, you don’t want to save a copy of the iCloud data onto your iPhone before signing out.

Everything you’re removing from your iPhone is stored on the iCloud server anyway, and you’re going to be signing back in to iCloud shortly, so you will get it all back very soon. So, sign out, and DON’T keep a copy of the iCloud data on your iPhone. Rest easy, it’s still on the iCloud server. You’ll see a message about “Removing iCloud Data.” Don’t worry you’re removing iCloud data from your iPhone, not from the server. (Don’t save a copy “just to be safe.” If you do save a copy of your iCloud data on your iPhone you’ll end up with duplicates and a big mess when you turn iCloud back on later. So don’t do that.)

  • Turn your iPhone off. Then turn it back on.
  • Go to the Settings. Resist temptation: do NOT “Sign in to your iPhone” at the top of the screen. Instead, scroll down to Messages, and sign in with your Apple ID credentials there. This is made a bit more difficult than it has to be due to there being no place to put your password. That’s OK– put in your Apple ID, then tap the Return key. That’s what produces the password box. Put in your password and then tap Sign In. In a moment– possibly after adding a six-digit two-factor authentication code– your phone should, probably, possibly, hopefully, indicate that iMessage is on, with NO message about “Waiting for activation.”
  • As long as you’re at it, go to FaceTime settings (Settings/FaceTime) and sign in with your Apple ID there too. Like iMessage, FaceTime should turn on without a “Waiting for activation” message.
  • Now go back to the first screen of Settings, tap “Sign in to your iPhone,” and sign in (same as above, you will have to tap Return after entering your Apple ID, otherwise you will never see the password box). Check that your iCloud settings are the same as they were before you signed out of iCloud, and correct them if they aren’t. You’re done!
After turning on iMessage, sign in to your iPhone.
After turning on iMessage, sign in to your iPhone

Just One More Thing

In iCloud settings, you probably want to turn ON Messages. With Messages in iCloud turned on, if you delete a text message from your iPhone, it will also delete from your other devices (Mac, iPad) that have Messages in iCloud turned on. That’s pretty handy.

Messages in iCloud turned on.
Messages in iCloud turned on

This is a new-ish feature– your iPhone has to be on 11.4 or later, and your Mac needs to be on 10.13.4 or later, otherwise the feature isn’t even there for you to turn on. It you have the option, you probably want to turn it on. I have an article about that here.


So, did it work? Let me know in the comments. If it did work, please share this article with your Facebook and Twitter friends. As far as I know, this method has not been published anywhere else on the web, and a lot of people have this problem. Help spread the word. Thanks to my friend Andrea for having faith that I’d figure it out for her when she had this problem.

How to forward (or delete) part of a text message conversation on an iPhone or iPad

Updated October 5th, 2020.

Every so often, for one reason or another you want to forward (or delete) part of a text message conversation from your iPhone. Not the entire conversation, just part of it. Maybe just one or two messages (maybe pictures). Here’s how you do it. (Here’s how you delete part of a Messages conversation on a Mac.)

Note: if you want to delete an entire conversation you simply swipe left on the conversation itself and then tap “Delete.” If you just want to delete every text message that is more than a year old (maybe you’re a football coach being investigated by the NCAA), go to Settings/Messages and set it to “Keep Messages” for 1 year.

Deleting part of a text message conversation

To delete a single message from a text message conversation on an iPhone or iPad, open the conversation so you’re looking at the messages. It will look something like this:

Representative text message conversation
Representative text message conversation

Tap and hold on the message you want to delete. You’ll see a few things pop up, including “More…” at the bottom. Tap “More…”

Text message showing special menu
Text message on an iPhone, after tapping and holding.

Now you see the conversation with everything shifted to the right, leaving space for a little circle to the left of each message. The circle next to the message you tapped on will be checked.

One message checked for deleting

Notice the trash can icon at the bottom left. Tap that to delete the message. Tap a confirming “Delete Message” button and you’re all set.

Confirm delete...
Confirm Delete

Note: after tapping “More…” you’re able to tap and put a check mark next to as many messages as you wish, and delete them all at once. See below.

Multiple messages selected

Caution: do not tap the “Delete All” button at the top left unless you really, really mean it.

If you have Messages in iCloud turned on, any deleting you do on one device will sync to your other devices, which makes things nice.

Forwarding part of a text message

Forwarding part of a text message works exactly the same way, right up to tapping the trash can icon. Instead of doing that, tap the “Forward” button at the bottom right, opposite the trash can. It looks like a curvy arrow pointing to the right. Tap that to forward the selected messages to someone else. You’ll choose who to forward the messages to in the box that pops up after you tap the Forward button.

Forwarding a text message
Forwarding a text message

Conclusion

I’ve found the ability to delete part of a text message, and to forward part of a text message, extremely powerful and handy. Give it a try and see for yourself.

How to sync text messages between your iPhone and your Mac

Updated October 4th, 2020.

UPDATE: things have changed a little since I wrote this article, and they’ve changed for the better! Apple now has something called “Messages in iCloud.” This means that you can now delete a message from your iPhone and it will be removed from your Mac automatically. It works in the other direction too. Previously– that is, when I first wrote this article– you could set things up so you received all of your text messages on both your iPhone and your Mac, but you had to delete them from both devices separately. Now, with Messages in the Cloud turned on (and that’s optional), Messages acts more like Mail– delete something from one device and it disappears from your other device.

Messages in iCloud requires at least macOS 10.13.4 and iOS 11.4. They weren’t invented when I first wrote this article. On the iPhone, you’ll find a new option in the iCloud section of the Settings, and it looks like this:

iPhone Settings: Messages in iCloud, switched on
iPhone Settings: Messages in iCloud, switched on

That’s just as you’d expect: Settings, iCloud, Messages turned on. On a Mac, it’s different— you don’t go to System Preferences / iCloud. The option to turn on Messages in iCloud is in the Messages app’s Preferences, so you start Messages, go to the Messages menu, come down to Preferences…, click on Accounts, and there you find the checkbox. Here it is:

Messages in iCloud settings panel in the Messages preferences.
The top arrow points to the Messages in iCloud checkbox. The bottom arrow points to your phone number.

You still need to do the things in the rest of this article, so keep reading. But now things really sync, both when messages are coming in, and when you are deleting them.

Below: the original article. Still important stuff.


It’s really handy to have your iPhone’s text messages show up on your Mac (and/or iPad). Start a texting conversation on your iPhone when you’re out, then continue it at home or work when you’re able to use your Mac (or iPad). Each device will have the complete conversation, and the other party will not know that you aren’t doing it all on your iPhone. Setting it up takes a couple of steps, and occasionally things stop working. In that case you’ll need to check on the settings again. This article tells you everything you need to know.

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If you’re not getting any of your text messages on your Mac or iPad, this article is for you. If you’re getting some, but not all, of your text messages on your Mac or iPad, this article is also for you!

iMessages are not text messages!

Technically, iMessages are not text messages, and text messages are not iMessages. “Real” text messages are handled by the phone company, and they are sent to devices with phone numbers (for example, to your iPhone). Real text messages appear in green on your iPhone in the Messages app. Apple’s “iMessage” service provides something that looks a lot like text messages, but with two important differences: iMessages are handled by Apple’s servers, so they don’t go through the phone company (which means the phone company can’t charge you for them), and they’re available on any device signed into your Apple ID. iMessages appear in blue on your devices.

iMessages will sync across all of your devices as long as they’re all signed into the same Apple ID. But text messages– the green ones– by default belong to your iPhone only, and they will not appear on your other devices, because text messages are tied to a phone number, which only your iPhone has. But will will fix that up shortly.

So you have two systems going at once: the phone company’s (green) text message system, and Apple’s (blue) iMessage system. The goal here is to tie these two systems together, and to show all of the messages, whether “text” or “iMessage,” all in the same Messages app. So how do we get the phone company’s text messages (sent to your phone number, on your iPhone) onto your Mac and iPad etc.? That’s what this article is about.

Note: your devices don’t really sync with each other. Rather, they sync with iCloud. There can be a little bit of a lag sometimes so you may notice messages appearing on one of your devices before the others. That’s just the way it goes– nothing for us to do about it.

Step 0: if you’ve never launched Messages on your Mac, launch it now. If you see this box, fill it in with your Apple ID and Apple ID password and then click “Sign in.”

Messages on the Mac initial settings
Messages on the Mac initial settings

Step 1: On your iPhone, go to Settings, then Messages. iMessage has to be ON. If it’s already on, but you’re not getting text messages onto your Mac, switch it off. Then switch it on. You’ll then see something that says “Use your Apple ID for iMessage.” Tap that, then enter your Apple ID and password. Signing in with your Apple ID is key to tieing your devices together. (It’s also often the step that people miss.)

Use your Apple ID for iMessage
Use your Apple ID for iMessage

Step 2: On your Mac, launch the Messages app (in the Dock by default) and go to Messages/Preferences… Click “Accounts.” You may see more than one account, but one of them should say “iMessage” underneath it. Click it, and be sure the checkbox for “Enable this account” (under Apple ID) is checked. If it’s not checked, check it. If you’re asked for a password, put it in– this is the Apple ID password that’s needed. 
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Messages Settings on Mac
Messages Settings on Mac

(You may notice that you DON’T see your iPhone’s phone number in the list where it says “You can be reached for messages at,” If it’s there, but unchecked, check it. If it’s not there, don’t worry, we are about to fix that.)

Step 3: Back on your iPhone, in Settings/Messages, tap “Text Message Forwarding.” You won’t see “Text Message Forwarding” if you don’t have iMessage switched on, and if you haven’t signed into iMessage using your Apple ID.

Having trouble switching on iMessage on your iPhone? Are you stuck “Waiting for activation”? If so, read my article “How to fix iMessage ‘Waiting for Activation’ on iPhone.”

With iMessage turned on on your iPhone, and with your iPhone signed into the Apple ID for iMessage, you should see the names of your devices (Christian’s iMac, Christian’s iPad, etc) when you tap “Text Message Forwarding.” If you read the fine print at the top of the pane that appears it will really tell the story: “Allow these devices to send and receive text messages from this iPhone.” YES! That’s what we want– we want “text messages” (the green ones– from the phone company) to appear on the Mac, and the iPad, and whatever. So we forward them. If we don’t do this, we only see blue (iMessage) messages on our devices that aren’t iPhones.

So, in Text Message Forwarding, slide the switch to “On” for each device. You might have to tap where it says “Apple ID” at the top of the screen– if it doesn’t show your Apple ID at the top, in blue, tap and enter your Apple ID and password one more time.

Use Apple ID for iMessage/Text Message Forwarding
Use Apple ID for iMessage/Text Message Forwarding

Note: you might think it makes sense to check everything under “You can be reached by iMessage at,” but that can lead to confusion when your recipients ask you why you are texting them from an email address. Better to uncheck everything but the phone number, on each devices.

And that’s it! If all went well, each of your devices will show all of your incoming messages, and show all of your sent ones. During the setting-up process you are bound to see notifications on various devices saying something like “Your Apple ID was used to sign into an iMac in Santa Monica, California” (except the location will be your location, not mine). That’s fine, and expected. That’s just us turning things on.

Bonus tip #1: on your Mac, double-click a conversation in Messages’ left-hand pane. That opens the conversation in its own window. That way, you can keep key conversations in view.

Bonus tip #2: on your Mac, try dragging a picture from one conversation into another. Just click and hold on the picture, then drag onto the other conversation. You can drag it from one conversation right onto the other, in Messages’ left-hand pane.

Bonus tip #3: on your Mac, try dragging a picture (or other document) from your desktop right into the area where you’d ordinarily be typing a message. Or just drag it onto the conversation– anywhere on it! So easy.

Any questions? Ask away— that’s what I’m here for. Did this help you? Tell a friend (use the sharing buttons).

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