diff --git a/Pods b/Pods
index 7753c413d..6d307f510 160000
--- a/Pods
+++ b/Pods
@@ -1 +1 @@
-Subproject commit 7753c413dc4efcfdab0e5f41e3245dd547dada7c
+Subproject commit 6d307f51039509e814d70c48527f69f7b850e6da
diff --git a/Signal/src/ViewControllers/ConversationView/ConversationViewController.m b/Signal/src/ViewControllers/ConversationView/ConversationViewController.m
index 2e3b7a141..ca91b9a16 100644
--- a/Signal/src/ViewControllers/ConversationView/ConversationViewController.m
+++ b/Signal/src/ViewControllers/ConversationView/ConversationViewController.m
@@ -3922,6 +3922,12 @@ typedef enum : NSUInteger {
 
         BOOL didAddToProfileWhitelist = [ThreadUtil addThreadToProfileWhitelistIfEmptyContactThread:self.thread];
 
+        if ([self.thread isKindOfClass:TSContactThread.class]) {
+            [LKStorage writeSyncWithBlock:^(YapDatabaseReadWriteTransaction *transaction) {
+                [LKSessionManagementProtocol sendSessionRequestIfNeededToPublicKey:self.thread.contactIdentifier transaction:transaction];
+            } error:nil];
+        }
+
         __block TSOutgoingMessage *message;
         [self.uiDatabaseConnection readWithBlock:^(YapDatabaseReadTransaction *_Nonnull transaction) {
             message = [ThreadUtil enqueueMessageWithText:messageText
@@ -4507,6 +4513,12 @@ typedef enum : NSUInteger {
         return;
     }
 
+    if ([self.thread isKindOfClass:TSContactThread.class]) {
+        [LKStorage writeSyncWithBlock:^(YapDatabaseReadWriteTransaction *transaction) {
+            [LKSessionManagementProtocol sendSessionRequestIfNeededToPublicKey:self.thread.contactIdentifier transaction:transaction];
+        } error:nil];
+    }
+
     // Limit outgoing text messages to 16kb.
     //
     // We convert large text messages to attachments
diff --git a/SignalServiceKit/src/Loki/Protocol/Session Management/SessionManagementProtocol.swift b/SignalServiceKit/src/Loki/Protocol/Session Management/SessionManagementProtocol.swift
index 0d6fd1d98..7bd5f5560 100644
--- a/SignalServiceKit/src/Loki/Protocol/Session Management/SessionManagementProtocol.swift	
+++ b/SignalServiceKit/src/Loki/Protocol/Session Management/SessionManagementProtocol.swift	
@@ -60,9 +60,11 @@ public final class SessionManagementProtocol : NSObject {
 
     // MARK: - Sending
 
-    @objc(shouldUseFallbackEncryptionForMessage:)
-    public static func shouldUseFallbackEncryption(for message: TSOutgoingMessage) -> Bool {
-        return true
+    @objc(shouldUseFallbackEncryptionForMessage:recipientID:transaction:)
+    public static func shouldUseFallbackEncryption(for message: TSOutgoingMessage, recipientID: String, transaction: YapDatabaseReadWriteTransaction) -> Bool {
+        if message is SessionRequestMessage { return true }
+        else if let message = message as? DeviceLinkMessage, message.kind == .request { return true }
+        return !storage.containsSession(recipientID, deviceId: Int32(OWSDevicePrimaryDeviceId), protocolContext: transaction)
     }
 
     private static func hasSentSessionRequestExpired(for publicKey: String) -> Bool {
@@ -71,6 +73,7 @@ public final class SessionManagementProtocol : NSObject {
         return NSDate.ows_millisecondTimeStamp() > expiration
     }
 
+    @objc(sendSessionRequestIfNeededToPublicKey:transaction:)
     public static func sendSessionRequestIfNeeded(to publicKey: String, using transaction: YapDatabaseReadWriteTransaction) {
         // It's never necessary to establish a session with self
         guard publicKey != getUserHexEncodedPublicKey() else { return }
@@ -93,9 +96,6 @@ public final class SessionManagementProtocol : NSObject {
         let sessionRequestMessage = SessionRequestMessage(thread: thread)
         let messageSenderJobQueue = SSKEnvironment.shared.messageSenderJobQueue
         messageSenderJobQueue.add(message: sessionRequestMessage, transaction: transaction)
-
-//        aushfiuasfhiujoasf
-        // TODO: Handle failure
     }
 
     @objc(sendNullMessageToPublicKey:transaction:)
diff --git a/SignalServiceKit/src/Messages/OWSMessageSender.m b/SignalServiceKit/src/Messages/OWSMessageSender.m
index 0cf86f314..8911a2354 100644
--- a/SignalServiceKit/src/Messages/OWSMessageSender.m
+++ b/SignalServiceKit/src/Messages/OWSMessageSender.m
@@ -1433,7 +1433,10 @@ NSString *const OWSMessageSenderRateLimitedException = @"RateLimitedException";
         messageSend.isUDSend);
 
     @try {
-        BOOL isSessionRequired = ![LKSessionManagementProtocol shouldUseFallbackEncryptionForMessage:messageSend.message];
+        __block BOOL isSessionRequired;
+        [LKStorage writeSyncWithBlock:^(YapDatabaseReadWriteTransaction *transaction) {
+            isSessionRequired = ![LKSessionManagementProtocol shouldUseFallbackEncryptionForMessage:messageSend.message recipientID:recipientID transaction:transaction];
+        } error:nil];
         if (isSessionRequired) {
             BOOL hasSession = [self throws_ensureRecipientHasSessionForMessageSend:messageSend recipientID:recipientID deviceId:@(OWSDevicePrimaryDeviceId)];
 
@@ -1634,7 +1637,7 @@ NSString *const OWSMessageSenderRateLimitedException = @"RateLimitedException";
         // • Alice receives this, sets up her Signal cipher session locally, and sends any subsequent messages
         //   using Signal encryption.
 
-        BOOL shouldUseFallbackEncryption = [LKSessionManagementProtocol shouldUseFallbackEncryptionForMessage:message];
+        BOOL shouldUseFallbackEncryption = [LKSessionManagementProtocol shouldUseFallbackEncryptionForMessage:message recipientID:recipientID transaction:transaction];
 
         serializedMessage = [secretCipher throwswrapped_encryptMessageWithRecipientPublicKey:recipientID
                                                                                     deviceID:@(OWSDevicePrimaryDeviceId).intValue
diff --git a/SignalServiceKit/src/Network/MessageSenderJobQueue.swift b/SignalServiceKit/src/Network/MessageSenderJobQueue.swift
index 324e8390c..9a875cb07 100644
--- a/SignalServiceKit/src/Network/MessageSenderJobQueue.swift
+++ b/SignalServiceKit/src/Network/MessageSenderJobQueue.swift
@@ -203,7 +203,16 @@ public class MessageSenderOperation: OWSOperation, DurableOperation {
     }
 
     override public func didReportError(_ error: Error) {
+        let message = self.message
+        var isFailedSessionRequest = false
+        if message is SessionRequestMessage, let publicKey = message.thread.contactIdentifier() {
+            isFailedSessionRequest = (Storage.getSessionRequestSentTimestamp(for: publicKey) == message.timestamp)
+        }
         try! Storage.writeSync { transaction in
+            if isFailedSessionRequest, let publicKey = message.thread.contactIdentifier() {
+                Storage.setSessionRequestSentTimestamp(for: publicKey, to: 0, using: transaction)
+            }
+
             self.durableOperationDelegate?.durableOperation(self, didReportError: error, transaction: transaction)
         }
     }
@@ -225,7 +234,16 @@ public class MessageSenderOperation: OWSOperation, DurableOperation {
     }
 
     override public func didFail(error: Error) {
+        let message = self.message
+        var isFailedSessionRequest = false
+        if message is SessionRequestMessage, let publicKey = message.thread.contactIdentifier() {
+            isFailedSessionRequest = (Storage.getSessionRequestSentTimestamp(for: publicKey) == message.timestamp)
+        }
         try! Storage.writeSync { transaction in
+            if isFailedSessionRequest, let publicKey = message.thread.contactIdentifier() {
+                Storage.setSessionRequestSentTimestamp(for: publicKey, to: 0, using: transaction)
+            }
+
             self.durableOperationDelegate?.durableOperation(self, didFailWithError: error, transaction: transaction)
 
             self.message.update(sendingError: error, transaction: transaction)