diff --git a/SignalServiceKit/src/Loki/Protocol/Friend Requests/FriendRequestProtocol.swift b/SignalServiceKit/src/Loki/Protocol/Friend Requests/FriendRequestProtocol.swift
index 3d1acd827..1d2faa4c8 100644
--- a/SignalServiceKit/src/Loki/Protocol/Friend Requests/FriendRequestProtocol.swift	
+++ b/SignalServiceKit/src/Loki/Protocol/Friend Requests/FriendRequestProtocol.swift	
@@ -60,6 +60,7 @@ public final class FriendRequestProtocol : NSObject {
         // Accept all outstanding friend requests associated with this user and try to establish sessions with the
         // subset of their devices that haven't sent a friend request.
         let linkedDeviceThreads = LokiDatabaseUtilities.getLinkedDeviceThreads(for: hexEncodedPublicKey, in: transaction) // This doesn't create new threads if they don't exist yet
+        // FIXME: Capture send failures
         for thread in linkedDeviceThreads {
             if thread.hasPendingFriendRequest {
                 sendFriendRequestAcceptanceMessage(to: thread.contactIdentifier(), in: thread, using: transaction) // NOT hexEncodedPublicKey
diff --git a/SignalServiceKit/src/Loki/Protocol/Multi Device/MultiDeviceProtocol.swift b/SignalServiceKit/src/Loki/Protocol/Multi Device/MultiDeviceProtocol.swift
index b332eea9f..725fb034f 100644
--- a/SignalServiceKit/src/Loki/Protocol/Multi Device/MultiDeviceProtocol.swift	
+++ b/SignalServiceKit/src/Loki/Protocol/Multi Device/MultiDeviceProtocol.swift	
@@ -41,7 +41,7 @@ public final class MultiDeviceProtocol : NSObject {
         return !(message is DeviceLinkMessage) && !message.thread.isGroupThread()
     }
 
-    private static func copy(_ messageSend: OWSMessageSend, for destination: MultiDeviceDestination, with seal: Resolver<TSContactThread>) -> OWSMessageSend {
+    private static func copy(_ messageSend: OWSMessageSend, for destination: MultiDeviceDestination, with seal: Resolver<Void>) -> OWSMessageSend {
         var recipient: SignalRecipient!
         storage.dbReadConnection.read { transaction in
             recipient = SignalRecipient.getOrBuildUnsavedRecipient(forRecipientId: destination.hexEncodedPublicKey, transaction: transaction)
@@ -49,47 +49,47 @@ public final class MultiDeviceProtocol : NSObject {
         // TODO: Why is it okay that the thread, sender certificate, etc. don't get changed?
         return OWSMessageSend(message: messageSend.message, thread: messageSend.thread, recipient: recipient,
             senderCertificate: messageSend.senderCertificate, udAccess: messageSend.udAccess, localNumber: messageSend.localNumber, success: {
-            seal.fulfill(messageSend.message.thread as! TSContactThread)
+            seal.fulfill(())
         }, failure: { error in
             seal.reject(error)
         })
     }
 
     private static func sendMessage(_ messageSend: OWSMessageSend, to destination: MultiDeviceDestination, in transaction: YapDatabaseReadTransaction) -> Promise<Void> {
-        let (promise, seal) = Promise<TSContactThread>.pending()
-        let message = messageSend.message
-        let messageSender = SSKEnvironment.shared.messageSender
-        promise.done(on: OWSDispatch.sendingQueue()) { thread in
+        let (threadPromise, threadPromiseSeal) = Promise<TSContactThread>.pending()
+        if let thread = TSContactThread.getWithContactId(destination.hexEncodedPublicKey, transaction: transaction) {
+            threadPromiseSeal.fulfill(thread)
+        } else {
+            // Dispatch async on the main queue to avoid nested write transactions
+            DispatchQueue.main.async {
+                storage.dbReadWriteConnection.readWrite { transaction in
+                    let thread = TSContactThread.getOrCreateThread(withContactId: destination.hexEncodedPublicKey, transaction: transaction)
+                    threadPromiseSeal.fulfill(thread)
+                }
+            }
+        }
+        return threadPromise.then(on: OWSDispatch.sendingQueue()) { thread -> Promise<Void> in
+            let message = messageSend.message
+            let messageSender = SSKEnvironment.shared.messageSender
+            let (promise, seal) = Promise<Void>.pending()
             let shouldSendAutoGeneratedFR = !thread.isContactFriend && !(message is FriendRequestMessage)
                 && message.shouldBeSaved() // shouldBeSaved indicates it isn't a transient message
             if !shouldSendAutoGeneratedFR {
                 let messageSendCopy = copy(messageSend, for: destination, with: seal)
                 messageSender.sendMessage(messageSendCopy)
             } else {
+                // Dispatch async on the main queue to avoid nested write transactions
                 DispatchQueue.main.async {
                     storage.dbReadWriteConnection.readWrite { transaction in
-                        getAutoGeneratedMultiDeviceFRMessageSend(for: destination.hexEncodedPublicKey, in: transaction)
+                        getAutoGeneratedMultiDeviceFRMessageSend(for: destination.hexEncodedPublicKey, in: transaction, seal: seal)
                         .done(on: OWSDispatch.sendingQueue()) { autoGeneratedFRMessageSend in
                             messageSender.sendMessage(autoGeneratedFRMessageSend)
                         }
                     }
                 }
             }
+            return promise
         }
-        promise.catch(on: OWSDispatch.sendingQueue()) { error in
-            print("[Loki] Couldn't get thread for destination: \(destination.hexEncodedPublicKey).")
-        }
-        if let thread = TSContactThread.getWithContactId(destination.hexEncodedPublicKey, transaction: transaction) {
-            seal.fulfill(thread)
-        } else {
-            DispatchQueue.main.async {
-                storage.dbReadWriteConnection.readWrite { transaction in
-                    let thread = TSContactThread.getOrCreateThread(withContactId: destination.hexEncodedPublicKey, transaction: transaction)
-                    seal.fulfill(thread)
-                }
-            }
-        }
-        return promise.map { _ in }
     }
 
     @objc(sendMessageToDestinationAndLinkedDevices:in:)
@@ -166,7 +166,7 @@ public final class MultiDeviceProtocol : NSObject {
         return AnyPromise.from(getAutoGeneratedMultiDeviceFRMessageSend(for: hexEncodedPublicKey, in: transaction))
     }
 
-    public static func getAutoGeneratedMultiDeviceFRMessageSend(for hexEncodedPublicKey: String, in transaction: YapDatabaseReadWriteTransaction) -> Promise<OWSMessageSend> {
+    public static func getAutoGeneratedMultiDeviceFRMessageSend(for hexEncodedPublicKey: String, in transaction: YapDatabaseReadWriteTransaction, seal externalSeal: Resolver<Void>? = nil) -> Promise<OWSMessageSend> {
         let thread = TSContactThread.getOrCreateThread(withContactId: hexEncodedPublicKey, transaction: transaction)
         let message = getAutoGeneratedMultiDeviceFRMessage(for: hexEncodedPublicKey, in: transaction)
         thread.friendRequestStatus = .requestSending
@@ -183,11 +183,15 @@ public final class MultiDeviceProtocol : NSObject {
             }
             let messageSend = OWSMessageSend(message: message, thread: thread, recipient: recipient, senderCertificate: senderCertificate,
                 udAccess: recipientUDAccess, localNumber: getUserHexEncodedPublicKey(), success: {
+                    externalSeal?.fulfill(())
+                    // Dispatch async on the main queue to avoid nested write transactions
                     DispatchQueue.main.async {
                         thread.friendRequestStatus = .requestSent
                         thread.save()
                     }
-            }, failure: { _ in
+            }, failure: { error in
+                externalSeal?.reject(error)
+                // Dispatch async on the main queue to avoid nested write transactions
                 DispatchQueue.main.async {
                     thread.friendRequestStatus = .none
                     thread.save()