A text to an Android contact, or occasionally even to another iPhone user, sits with a spinner and then shows a red "Not Delivered" in Messages on Mac after updating to Golden Gate, while the identical message sends fine from the same Apple ID's iPhone. This has been reported on Golden Gate's own support forums, but the mechanism behind it long predates this release, and understanding that mechanism is most of the fix.

How SMS and RCS on a Mac actually works

A Mac has no SIM card, no carrier account, and no direct way to send SMS or RCS. Every green-bubble message you send from Messages on a Mac is quietly relayed through a paired iPhone using a feature called Text Message Forwarding. The Mac sends the message to the iPhone over your Apple ID and local network, the iPhone hands it to your carrier, and the carrier delivers it. iMessage, the blue-bubble kind, works differently and doesn't depend on this relay at all, which is an important diagnostic clue: if iMessage to other Apple users works fine but green-bubble texts fail, the problem is specifically in this relay, not in Messages or macOS generally.

RCS (Rich Communication Services), the modern replacement for plain SMS when texting Android users, uses the exact same relay mechanism, registered through your iPhone's phone number rather than anything the Mac itself can register independently.

Fix 1: confirm the bridge is actually set up

Before troubleshooting anything deeper, confirm the basic requirements are actually met, since any one missing piece produces exactly this symptom:

  • An iPhone running a current iOS version, signed into the same Apple ID as your Mac.
  • Text Message Forwarding enabled for this specific Mac. On the iPhone: Settings > Messages > Text Message Forwarding, and confirm this Mac's toggle is on.
  • If your Mac doesn't appear in that list at all, Find My needs to be enabled for the Mac; it's a prerequisite for the Mac showing up as a forwarding target.
  • Both devices connected to the internet, and ideally on the same Wi-Fi network, although this isn't always strictly required.

Fix 2: re-establish the bridge from both ends

If everything above looks correctly configured but it's still failing, the relay itself has likely gotten into a stale state, which a clean re-link usually resolves:

  1. On the iPhone: Settings > Messages > Text Message Forwarding, turn this Mac's toggle off.
  2. On the Mac: open Messages > Settings > iMessage, and sign out of iMessage entirely.
  3. Restart both devices.
  4. On the Mac, sign back into Messages.
  5. On the iPhone, turn Text Message Forwarding for this Mac back on. You'll see a verification code appear on the Mac; enter it on the iPhone to confirm the pairing.
  6. Send a test SMS or RCS message from the Mac.

This resets the entire relay relationship rather than patching around a symptom, and resolves the majority of "Not Delivered" cases that aren't specific to one contact.

Fix 3: delete and recreate the specific failing conversation

If the problem is isolated to one specific contact or conversation thread, rather than every green-bubble message, the conversation's own local record is more likely to be the cause than the device-level bridge:

  1. In Messages on the Mac, open the failing conversation.
  2. Delete the conversation (right-click it in the sidebar list, or use the Edit menu).
  3. Go to Messages > Edit > Show Recently Deleted, and permanently delete it from there as well, rather than leaving it recoverable.
  4. Start a fresh new message to that same contact and test again.

Corrupted or malformed data tied to one specific conversation thread is a known, if less common, cause, and this fully clears whatever state that thread had accumulated.

Fix 4: for one contact only, check the contact entry itself

If a message succeeds as RCS to some contacts but silently fails for exactly one person, the issue is sometimes in how that specific contact's phone number is formatted, rather than in Messages or the relay at all:

  • Open that contact in Contacts and check whether their number includes a country code. Reports describe RCS specifically failing or defaulting to SMS when a number is stored without one, and succeeding again once the full international format is added.
  • As a more drastic test, some people have resolved a single stuck contact by removing just the phone number from that contact (not deleting the contact entirely), then re-adding it fresh.

Advanced: a malformed database record

For a conversation that keeps failing specifically with "Not Delivered" while every other SMS and RCS conversation on the same Mac works fine, there is a documented, more technical cause worth knowing about even if you don't attempt the fix yourself: a malformed value in the last_addressed_handle field of the specific chat record inside Messages' own local database (~/Library/Messages/chat.db). This has been identified by at least one user who compared a working SMS conversation's database record against a failing one directly. Editing this database file directly carries real risk to your message history if done incorrectly, so Fix 3 above, deleting and recreating the conversation through Messages itself rather than editing the database by hand, achieves the same practical result far more safely for almost everyone.

Is this actually a Golden Gate regression?

This exact symptom, RCS and SMS failing to deliver specifically from a Mac or iPad while working fine from the paired iPhone, has been reported following multiple recent iOS and macOS releases, not uniquely this one. What is specific to Golden Gate is simply that the complaint has resurfaced on its own support forum. If you've just upgraded and this started immediately afterward, re-establishing the device pairing with Fix 2 is the right first move regardless of whether the root trigger was something Golden Gate changed or simply the normal disruption any major update can cause to a relay relationship like this one.

The short version

  • A Mac cannot send SMS or RCS on its own; every green-bubble message is relayed through a paired iPhone via Text Message Forwarding.
  • If iMessage works but SMS/RCS doesn't, the relay itself is almost always the cause, not Messages or macOS generally.
  • Turning Text Message Forwarding off and back on, with a sign-out and restart on both devices, resolves most cases.
  • A single stuck contact is more often a formatting or local-database issue specific to that conversation; deleting and recreating the conversation is the safe fix.