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.

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

This used to work: Jeff used to send voice memos of similar length to the same recipient using the same iPhone, and never an error. But now: “Attachment is Too Long.”

Note: this problem was only happening for a “green” recipient, the kind who isn’t using an iPhone or an iPad or a Mac to get text messages. Green messages go through the phone company– they are true “text messages.” Blue messages go through Apple’s iMessage system, which is better, and we were able to send the voice memo to blue recipients, but in this case our recipient was a greenie.

One option was to buy the recipient an iPhone. Sort of a pricey way to go. There had to be something we could do at our end.

We (I) had high hopes when iOS 14.3 came out, because the problem first surfaced after updating to iOS 14. (Everything worked fine in iOS 13.x.) I installed 14.3 here on my extra iPhone and tried sending the same “too long” attachment that we hadn’t been able to send in iOS 14.2, and… it still didn’t work. What a drag.

We did get “Siri animal sounds” in the iOS 14.3 update… try asking Siri “What sound does a cow make.”

The Answer

After a lot of Google searches, and a lot of head-scratching, I came to the conclusion that the problem had something to do with the cellular carrier, because when we’re sending green text messages they’re going through the cell phone system, not through WiFi. I thought maybe resetting the cellular settings would work, but that option– which used to be in Settings/Cellular– isn’t there in iOS 14.3.

Fortunately, there’s still a way to reset the cellular settings; it just isn’t in the Cellular section of the Settings app, and it isn’t called “Reset Cellular Settings.” Now it’s called “Reset Network Settings,” and you get there by going to Settings, then General, then Reset.

When you tap “Reset Network Settings” you’re asked to enter your iPhone’s unlock passcode, and then you’re asked to confirm that you really want to reset network settings.

All we wanted here was to reset the cellular settings, but now we’re going to wipe out ALL network settings, including WiFi passwords… which sounds like something we don’t want to do! But… if you’re using the iCloud Keychain, your passwords are remembered in iCloud, so you’ll get them right back. We’re wiping the passwords off this particular iPhone, not off of iCloud.

Not sure whether you’re using the iCloud Keychain? Better check before you reset the network settings, because if you don’t have the iCloud Keychain set up in advance you’ll have to enter passwords for WiFi networks you’ve previously joined, and that’s no fun.

Here’s how you check that you’re saving passwords in the iCloud Keychain.

Go to Settings, then tap your name at the top, then iCloud. Be sure Keychain is turned on.

Back to our problem…

Once you know that you’ll get your network passwords back via iCloud you can go ahead with resetting the network settings. Then try sending your “Too Long” attachment again. Over here, it worked right away.

Conclusion

We learned something! Resetting network settings might solve other mysterious problems one day. I’ll remember this.

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