Sender Key: Prepare for production

protos/UnidentifiedDelivery.proto

@@ -43,14 +43,14 @@ message UnidentifiedSenderMessage {
         }
 
         enum ContentHint {
-            // Our parser does not handle reserved in enums: DESKTOP-1569
+            // Show an error immediately; it was important but we can't retry.
-            // reserved 0; // A content hint of "default" should never be encoded.
+            DEFAULT = 0;
         
-            // Do not insert an error.
+            // Sender will try to resend; delay any error UI if possible
-            SUPPLEMENTARY = 1; 
+            RESENDABLE = 1;
 
-            // Put an invisible placeholder in the chat (using the groupId from the sealed sender envelope if available) and delay showing an error until later.
+            // Don't show any error UI at all; this is something sent implicitly like a typing message or a receipt
-            RESENDABLE    = 2;
+            IMPLICIT   = 2;
         }
 
         optional Type              type              = 1;

ts/RemoteConfig.ts

@@ -11,7 +11,10 @@ export type ConfigKeyType =
   | 'desktop.gv2'
   | 'desktop.mandatoryProfileSharing'
   | 'desktop.messageRequests'
+  | 'desktop.retryReceiptLifespan'
+  | 'desktop.retryRespondMaxAge'
   | 'desktop.screensharing2'
+  | 'desktop.sendSenderKey'
   | 'desktop.storage'
   | 'desktop.storageWrite3'
   | 'desktop.worksAtSignal'

ts/background.ts

@@ -425,30 +425,6 @@ export async function startApp(): Promise<void> {
     first = false;
 
     cleanupSessionResets();
-    const retryPlaceholders = new window.Signal.Util.RetryPlaceholders();
-    window.Signal.Services.retryPlaceholders = retryPlaceholders;
-
-    setInterval(async () => {
-      const expired = await retryPlaceholders.getExpiredAndRemove();
-      window.log.info(
-        `retryPlaceholders/interval: Found ${expired.length} expired items`
-      );
-      expired.forEach(item => {
-        const { conversationId, senderUuid } = item;
-        const conversation = window.ConversationController.get(conversationId);
-        if (conversation) {
-          const receivedAt = Date.now();
-          const receivedAtCounter = window.Signal.Util.incrementMessageCounter();
-          conversation.queueJob(() =>
-            conversation.addDeliveryIssue({
-              receivedAt,
-              receivedAtCounter,
-              senderUuid,
-            })
-          );
-        }
-      });
-    }, FIVE_MINUTES);
 
     // These make key operations available to IPC handlers created in preload.js
     window.Events = {
@@ -835,6 +811,46 @@ export async function startApp(): Promise<void> {
     // we generate on load of each convo.
     window.Signal.RemoteConfig.initRemoteConfig();
 
+    let retryReceiptLifespan: number | undefined;
+    try {
+      retryReceiptLifespan = parseIntOrThrow(
+        window.Signal.RemoteConfig.getValue('desktop.retryReceiptLifespan'),
+        'retryReceiptLifeSpan'
+      );
+    } catch (error) {
+      window.log.warn(
+        'Failed to parse integer out of desktop.retryReceiptLifespan feature flag',
+        error && error.stack ? error.stack : error
+      );
+    }
+
+    const retryPlaceholders = new window.Signal.Util.RetryPlaceholders({
+      retryReceiptLifespan,
+    });
+    window.Signal.Services.retryPlaceholders = retryPlaceholders;
+
+    setInterval(async () => {
+      const expired = await retryPlaceholders.getExpiredAndRemove();
+      window.log.info(
+        `retryPlaceholders/interval: Found ${expired.length} expired items`
+      );
+      expired.forEach(item => {
+        const { conversationId, senderUuid } = item;
+        const conversation = window.ConversationController.get(conversationId);
+        if (conversation) {
+          const receivedAt = Date.now();
+          const receivedAtCounter = window.Signal.Util.incrementMessageCounter();
+          conversation.queueJob(() =>
+            conversation.addDeliveryIssue({
+              receivedAt,
+              receivedAtCounter,
+              senderUuid,
+            })
+          );
+        }
+      });
+    }, FIVE_MINUTES);
+
     try {
       await Promise.all([
         window.ConversationController.load(),
@@ -2148,7 +2164,9 @@ export async function startApp(): Promise<void> {
           await server.registerCapabilities({
             'gv2-3': true,
             'gv1-migration': true,
-            senderKey: false,
+            senderKey: window.Signal.RemoteConfig.isEnabled(
+              'desktop.sendSenderKey'
+            ),
           });
         } catch (error) {
           window.log.error(
@@ -3408,13 +3426,106 @@ export async function startApp(): Promise<void> {
     return false;
   }
 
+  async function archiveSessionOnMatch({
+    requesterUuid,
+    requesterDevice,
+    senderDevice,
+  }: RetryRequestType): Promise<void> {
+    const ourDeviceId = parseIntOrThrow(
+      window.textsecure.storage.user.getDeviceId(),
+      'archiveSessionOnMatch/getDeviceId'
+    );
+    if (ourDeviceId === senderDevice) {
+      const address = `${requesterUuid}.${requesterDevice}`;
+      window.log.info(
+        'archiveSessionOnMatch: Devices match, archiving session'
+      );
+      await window.textsecure.storage.protocol.archiveSession(address);
+    }
+  }
+
+  async function sendDistributionMessageOrNullMessage(
+    options: RetryRequestType
+  ): Promise<void> {
+    const { groupId, requesterUuid } = options;
+    let sentDistributionMessage = false;
+    window.log.info('sendDistributionMessageOrNullMessage: Starting', {
+      groupId: groupId ? `groupv2(${groupId})` : undefined,
+      requesterUuid,
+    });
+
+    await archiveSessionOnMatch(options);
+
+    const conversation = window.ConversationController.getOrCreate(
+      requesterUuid,
+      'private'
+    );
+
+    if (groupId) {
+      const group = window.ConversationController.get(groupId);
+      const distributionId = group?.get('senderKeyInfo')?.distributionId;
+
+      if (group && distributionId) {
+        window.log.info(
+          'sendDistributionMessageOrNullMessage: Found matching group, sending sender key distribution message'
+        );
+
+        try {
+          const {
+            ContentHint,
+          } = window.textsecure.protobuf.UnidentifiedSenderMessage.Message;
+
+          const result = await window.textsecure.messaging.sendSenderKeyDistributionMessage(
+            {
+              contentHint: ContentHint.DEFAULT,
+              distributionId,
+              groupId,
+              identifiers: [requesterUuid],
+            }
+          );
+          if (result.errors && result.errors.length > 0) {
+            throw result.errors[0];
+          }
+          sentDistributionMessage = true;
+        } catch (error) {
+          window.log.error(
+            'sendDistributionMessageOrNullMessage: Failed to send sender key distribution message',
+            error && error.stack ? error.stack : error
+          );
+        }
+      }
+    }
+
+    if (!sentDistributionMessage) {
+      window.log.info(
+        'sendDistributionMessageOrNullMessage: Did not send distribution message, sending null message'
+      );
+
+      try {
+        const sendOptions = await conversation.getSendOptions();
+        const result = await window.textsecure.messaging.sendNullMessage(
+          { uuid: requesterUuid },
+          sendOptions
+        );
+        if (result.errors && result.errors.length > 0) {
+          throw result.errors[0];
+        }
+      } catch (error) {
+        window.log.error(
+          'maybeSendDistributionMessage: Failed to send null message',
+          error && error.stack ? error.stack : error
+        );
+      }
+    }
+  }
+
   async function onRetryRequest(event: RetryRequestEventType) {
     const { retryRequest } = event;
     const {
-      requesterUuid,
       requesterDevice,
-      sentAt,
+      requesterUuid,
       senderDevice,
+      sentAt,
     } = retryRequest;
     const logId = `${requesterUuid}.${requesterDevice} ${sentAt}-${senderDevice}`;
 
@@ -3447,6 +3558,7 @@ export async function startApp(): Promise<void> {
 
     if (!targetMessage) {
       window.log.info(`onRetryRequest/${logId}: Did not find message`);
+      await sendDistributionMessageOrNullMessage(retryRequest);
       return;
     }
 
@@ -3454,47 +3566,36 @@ export async function startApp(): Promise<void> {
       window.log.info(
         `onRetryRequest/${logId}: Message is erased, refusing to send again.`
       );
+      await sendDistributionMessageOrNullMessage(retryRequest);
       return;
     }
 
     const HOUR = 60 * 60 * 1000;
     const ONE_DAY = 24 * HOUR;
-    if (isOlderThan(sentAt, ONE_DAY)) {
+    let retryRespondMaxAge = ONE_DAY;
+    try {
+      retryRespondMaxAge = parseIntOrThrow(
+        window.Signal.RemoteConfig.getValue('desktop.retryRespondMaxAge'),
+        'retryRespondMaxAge'
+      );
+    } catch (error) {
+      window.log.warn(
+        `onRetryRequest/${logId}: Failed to parse integer from desktop.retryRespondMaxAge feature flag`,
+        error && error.stack ? error.stack : error
+      );
+    }
+
+    if (isOlderThan(sentAt, retryRespondMaxAge)) {
       window.log.info(
         `onRetryRequest/${logId}: Message is too old, refusing to send again.`
       );
+      await sendDistributionMessageOrNullMessage(retryRequest);
       return;
     }
 
-    const sentUnidentified = isInList(
-      requesterConversation,
-      targetMessage.get('unidentifiedDeliveries')
-    );
-    const wasDelivered = isInList(
-      requesterConversation,
-      targetMessage.get('delivered_to')
-    );
-    if (sentUnidentified && wasDelivered) {
-      window.log.info(
-        `onRetryRequest/${logId}: Message was sent sealed sender and was delivered, refusing to send again.`
-      );
-      return;
-    }
-
-    const ourDeviceId = parseIntOrThrow(
-      window.textsecure.storage.user.getDeviceId(),
-      'onRetryRequest/getDeviceId'
-    );
-    if (ourDeviceId === senderDevice) {
-      const address = `${requesterUuid}.${requesterDevice}`;
-      window.log.info(
-        `onRetryRequest/${logId}: Devices match, archiving session`
-      );
-      await window.textsecure.storage.protocol.archiveSession(address);
-    }
-
     window.log.info(`onRetryRequest/${logId}: Resending message`);
-    targetMessage.resend(requesterUuid);
+    await archiveSessionOnMatch(retryRequest);
+    await targetMessage.resend(requesterUuid);
   }
 
   type DecryptionErrorEventType = Event & {
@@ -3558,16 +3659,6 @@ export async function startApp(): Promise<void> {
     );
     const conversation = group || sender;
 
-    function immediatelyAddError() {
-      conversation.queueJob(async () => {
-        conversation.addDeliveryIssue({
-          receivedAt: receivedAtDate,
-          receivedAtCounter,
-          senderUuid,
-        });
-      });
-    }
-
     // 2. Send resend request
 
     if (!cipherTextBytes || !isNumber(cipherTextType)) {
@@ -3611,14 +3702,7 @@ export async function startApp(): Promise<void> {
 
     // 3. Determine how to represent this to the user. Three different options.
 
-    // This is a sync message of some kind that cannot be resent. Reset session but don't
+    // We believe that it could be successfully re-sent, so we'll add a placeholder.
-    //   show any UI for it.
-    if (contentHint === ContentHint.SUPPLEMENTARY) {
-      scheduleSessionReset(senderUuid, senderDevice);
-      return;
-    }
-
-    // If we request a re-send, it might just work out for us!
     if (contentHint === ContentHint.RESENDABLE) {
       const { retryPlaceholders } = window.Signal.Services;
       assert(retryPlaceholders, 'requestResend: adding placeholder');
@@ -3635,10 +3719,22 @@ export async function startApp(): Promise<void> {
       return;
     }
 
+    // This message cannot be resent. We'll show no error and trust the other side to
+    //   reset their session.
+    if (contentHint === ContentHint.IMPLICIT) {
+      return;
+    }
+
     window.log.warn(
       `requestResend/${logId}: No content hint, adding error immediately`
     );
-    immediatelyAddError();
+    conversation.queueJob(async () => {
+      conversation.addDeliveryIssue({
+        receivedAt: receivedAtDate,
+        receivedAtCounter,
+        senderUuid,
+      });
+    });
   }
 
   function scheduleSessionReset(senderUuid: string, senderDevice: number) {

ts/groups.ts

@@ -1322,7 +1322,7 @@ export async function modifyGroupV2({
               profileKey,
             },
             conversation,
-            ContentHint.SUPPLEMENTARY,
+            ContentHint.DEFAULT,
             sendOptions
           )
         );
@@ -1696,7 +1696,7 @@ export async function createGroupV2({
           profileKey,
         },
         conversation,
-        ContentHint.SUPPLEMENTARY,
+        ContentHint.DEFAULT,
         sendOptions
       ),
     timestamp,
@@ -2226,7 +2226,7 @@ export async function initiateMigrationToGroupV2(
           profileKey: ourProfileKey,
         },
         conversation,
-        ContentHint.SUPPLEMENTARY,
+        ContentHint.DEFAULT,
         sendOptions
       ),
     timestamp,

ts/models/conversations.ts

@@ -1201,7 +1201,7 @@ export class ConversationModel extends window.Backbone
             timestamp,
             groupMembers,
             contentMessage,
-            ContentHint.SUPPLEMENTARY,
+            ContentHint.IMPLICIT,
             undefined,
             {
               ...sendOptions,
@@ -1212,7 +1212,7 @@ export class ConversationModel extends window.Backbone
       } else {
         handleMessageSend(
           window.Signal.Util.sendContentMessageToGroup({
-            contentHint: ContentHint.SUPPLEMENTARY,
+            contentHint: ContentHint.IMPLICIT,
             contentMessage,
             conversation: this,
             online: true,
@@ -3289,7 +3289,7 @@ export class ConversationModel extends window.Backbone
             targetTimestamp,
             timestamp,
             undefined, // expireTimer
-            ContentHint.SUPPLEMENTARY,
+            ContentHint.DEFAULT,
             undefined, // groupId
             profileKey,
             options
@@ -3305,7 +3305,7 @@ export class ConversationModel extends window.Backbone
             profileKey,
           },
           this,
-          ContentHint.SUPPLEMENTARY,
+          ContentHint.DEFAULT,
           options
         );
       })();
@@ -3446,7 +3446,7 @@ export class ConversationModel extends window.Backbone
             undefined, // deletedForEveryoneTimestamp
             timestamp,
             expireTimer,
-            ContentHint.SUPPLEMENTARY,
+            ContentHint.DEFAULT,
             undefined, // groupId
             profileKey,
             options
@@ -3465,7 +3465,7 @@ export class ConversationModel extends window.Backbone
             profileKey,
           },
           this,
-          ContentHint.SUPPLEMENTARY,
+          ContentHint.DEFAULT,
           options
         );
       })();

ts/models/messages.ts

@@ -3601,9 +3601,13 @@ export class MessageModel extends window.Backbone.Model<MessageAttributesType> {
           conversationId,
           message.get('sent_at')
         );
-        if (item) {
+        if (item && item.wasOpened) {
           window.log.info(
-            `handleDataMessage: found retry placeholder. Updating ${message.idForLogging()} received_at/received_at_ms`
+            `handleDataMessage: found retry placeholder for ${message.idForLogging()}, but conversation was opened. No updates made.`
+          );
+        } else if (item) {
+          window.log.info(
+            `handleDataMessage: found retry placeholder for ${message.idForLogging()}. Updating received_at/received_at_ms`
           );
           message.set({
             received_at: item.receivedAtCounter,

ts/services/calling.ts

@@ -805,7 +805,7 @@ export class CallingClass {
         window.Signal.Util.sendToGroup(
           { groupCallUpdate: { eraId }, groupV2, timestamp },
           conversation,
-          ContentHint.SUPPLEMENTARY,
+          ContentHint.DEFAULT,
           sendOptions
         ),
       timestamp,

ts/test-both/util/retryPlaceholders_test.ts

@@ -2,9 +2,10 @@
 // SPDX-License-Identifier: AGPL-3.0-only
 
 import { assert } from 'chai';
+import sinon from 'sinon';
 
 import {
-  getOneHourAgo,
+  getDeltaIntoPast,
   RetryItemType,
   RetryPlaceholders,
   STORAGE_KEY,
@@ -13,15 +14,26 @@ import {
 /* eslint-disable @typescript-eslint/no-explicit-any */
 
 describe('RetryPlaceholders', () => {
+  const NOW = 1_000_000;
+  let clock: any;
+
   beforeEach(() => {
     window.storage.put(STORAGE_KEY, null);
+
+    clock = sinon.useFakeTimers({
+      now: NOW,
+    });
+  });
+
+  afterEach(() => {
+    clock.restore();
   });
 
   function getDefaultItem(): RetryItemType {
     return {
       conversationId: 'conversation-id',
-      sentAt: Date.now() - 10,
+      sentAt: NOW - 10,
-      receivedAt: Date.now() - 5,
+      receivedAt: NOW - 5,
       receivedAtCounter: 4,
       senderUuid: 'sender-uuid',
     };
@@ -87,11 +99,11 @@ describe('RetryPlaceholders', () => {
     it('returns soonest expiration given a list, and after add', async () => {
       const older = {
         ...getDefaultItem(),
-        receivedAt: Date.now(),
+        receivedAt: NOW,
       };
       const newer = {
         ...getDefaultItem(),
-        receivedAt: Date.now() + 10,
+        receivedAt: NOW + 10,
       };
       const items: Array<RetryItemType> = [older, newer];
       window.storage.put(STORAGE_KEY, items);
@@ -102,7 +114,7 @@ describe('RetryPlaceholders', () => {
 
       const oldest = {
         ...getDefaultItem(),
-        receivedAt: Date.now() - 5,
+        receivedAt: NOW - 5,
       };
 
       await placeholders.add(oldest);
@@ -115,11 +127,11 @@ describe('RetryPlaceholders', () => {
     it('does nothing if no item expired', async () => {
       const older = {
         ...getDefaultItem(),
-        receivedAt: Date.now() + 10,
+        receivedAt: NOW + 10,
       };
       const newer = {
         ...getDefaultItem(),
-        receivedAt: Date.now() + 15,
+        receivedAt: NOW + 15,
       };
       const items: Array<RetryItemType> = [older, newer];
       window.storage.put(STORAGE_KEY, items);
@@ -132,11 +144,11 @@ describe('RetryPlaceholders', () => {
     it('removes just one if expired', async () => {
       const older = {
         ...getDefaultItem(),
-        receivedAt: getOneHourAgo() - 1000,
+        receivedAt: getDeltaIntoPast() - 1000,
       };
       const newer = {
         ...getDefaultItem(),
-        receivedAt: Date.now() + 15,
+        receivedAt: NOW + 15,
       };
       const items: Array<RetryItemType> = [older, newer];
       window.storage.put(STORAGE_KEY, items);
@@ -150,11 +162,11 @@ describe('RetryPlaceholders', () => {
     it('removes all if expired', async () => {
       const older = {
         ...getDefaultItem(),
-        receivedAt: getOneHourAgo() - 1000,
+        receivedAt: getDeltaIntoPast() - 1000,
       };
       const newer = {
         ...getDefaultItem(),
-        receivedAt: getOneHourAgo() - 900,
+        receivedAt: getDeltaIntoPast() - 900,
       };
       const items: Array<RetryItemType> = [older, newer];
       window.storage.put(STORAGE_KEY, items);
@@ -169,7 +181,7 @@ describe('RetryPlaceholders', () => {
     });
   });
 
-  describe('#findByConversationAndRemove', () => {
+  describe('#findByConversationAndMarkOpened', () => {
     it('does nothing if no items found matching conversation', async () => {
       const older = {
         ...getDefaultItem(),
@@ -184,68 +196,101 @@ describe('RetryPlaceholders', () => {
 
       const placeholders = new RetryPlaceholders();
       assert.strictEqual(2, placeholders.getCount());
-      assert.deepEqual(
+      await placeholders.findByConversationAndMarkOpened('conversation-id-3');
-        [],
-        await placeholders.findByConversationAndRemove('conversation-id-3')
-      );
       assert.strictEqual(2, placeholders.getCount());
+
+      const saveItems = window.storage.get(STORAGE_KEY);
+      assert.deepEqual([older, newer], saveItems);
     });
-    it('removes all items matching conversation', async () => {
+    it('updates all items matching conversation', async () => {
       const convo1a = {
         ...getDefaultItem(),
         conversationId: 'conversation-id-1',
-        receivedAt: Date.now() - 5,
+        receivedAt: NOW - 5,
       };
       const convo1b = {
         ...getDefaultItem(),
         conversationId: 'conversation-id-1',
-        receivedAt: Date.now() - 4,
+        receivedAt: NOW - 4,
       };
       const convo2a = {
         ...getDefaultItem(),
         conversationId: 'conversation-id-2',
-        receivedAt: Date.now() + 15,
+        receivedAt: NOW + 15,
       };
       const items: Array<RetryItemType> = [convo1a, convo1b, convo2a];
       window.storage.put(STORAGE_KEY, items);
 
       const placeholders = new RetryPlaceholders();
       assert.strictEqual(3, placeholders.getCount());
+      await placeholders.findByConversationAndMarkOpened('conversation-id-1');
+      assert.strictEqual(3, placeholders.getCount());
+
+      const firstSaveItems = window.storage.get(STORAGE_KEY);
       assert.deepEqual(
-        [convo1a, convo1b],
+        [
-        await placeholders.findByConversationAndRemove('conversation-id-1')
+          {
+            ...convo1a,
+            wasOpened: true,
+          },
+          {
+            ...convo1b,
+            wasOpened: true,
+          },
+          convo2a,
+        ],
+        firstSaveItems
       );
-      assert.strictEqual(1, placeholders.getCount());
 
       const convo2b = {
         ...getDefaultItem(),
         conversationId: 'conversation-id-2',
-        receivedAt: Date.now() + 16,
+        receivedAt: NOW + 16,
       };
 
       await placeholders.add(convo2b);
-      assert.strictEqual(2, placeholders.getCount());
+      assert.strictEqual(4, placeholders.getCount());
+      await placeholders.findByConversationAndMarkOpened('conversation-id-2');
+      assert.strictEqual(4, placeholders.getCount());
+
+      const secondSaveItems = window.storage.get(STORAGE_KEY);
       assert.deepEqual(
-        [convo2a, convo2b],
+        [
-        await placeholders.findByConversationAndRemove('conversation-id-2')
+          {
+            ...convo1a,
+            wasOpened: true,
+          },
+          {
+            ...convo1b,
+            wasOpened: true,
+          },
+          {
+            ...convo2a,
+            wasOpened: true,
+          },
+          {
+            ...convo2b,
+            wasOpened: true,
+          },
+        ],
+        secondSaveItems
       );
-      assert.strictEqual(0, placeholders.getCount());
     });
   });
 
   describe('#findByMessageAndRemove', () => {
     it('does nothing if no item matching message found', async () => {
-      const sentAt = Date.now() - 20;
+      const sentAt = NOW - 20;
 
       const older = {
         ...getDefaultItem(),
         conversationId: 'conversation-id-1',
-        sentAt: Date.now() - 10,
+        sentAt: NOW - 10,
       };
       const newer = {
         ...getDefaultItem(),
         conversationId: 'conversation-id-1',
-        sentAt: Date.now() - 11,
+        sentAt: NOW - 11,
       };
       const items: Array<RetryItemType> = [older, newer];
       window.storage.put(STORAGE_KEY, items);
@@ -258,12 +303,12 @@ describe('RetryPlaceholders', () => {
       assert.strictEqual(2, placeholders.getCount());
     });
     it('removes the item matching message', async () => {
-      const sentAt = Date.now() - 20;
+      const sentAt = NOW - 20;
 
       const older = {
         ...getDefaultItem(),
         conversationId: 'conversation-id-1',
-        sentAt: Date.now() - 10,
+        sentAt: NOW - 10,
       };
       const newer = {
         ...getDefaultItem(),

ts/textsecure.d.ts

@@ -1411,7 +1411,8 @@ export declare namespace UnidentifiedSenderMessageClass.Message {
   }
 
   class ContentHint {
-    static SUPPLEMENTARY: number;
+    static DEFAULT: number;
     static RESENDABLE: number;
+    static IMPLICIT: number;
   }
 }

ts/textsecure/MessageReceiver.ts

@@ -93,6 +93,7 @@ export type DecryptionErrorType = z.infer<typeof decryptionErrorTypeSchema>;
 
 const retryRequestTypeSchema = z
   .object({
+    groupId: z.string().optional(),
     requesterUuid: z.string(),
     requesterDevice: z.number(),
     senderDevice: z.number(),
@@ -1757,10 +1758,11 @@ class MessageReceiverInner extends EventTarget {
 
     const event = new Event('retry-request');
     event.retryRequest = {
-      sentAt: request.timestamp(),
+      groupId: envelope.groupId,
-      requesterUuid: sourceUuid,
       requesterDevice: sourceDevice,
+      requesterUuid: sourceUuid,
       senderDevice: request.deviceId(),
+      sentAt: request.timestamp(),
     };
     await this.dispatchAndWait(event);
   }

ts/textsecure/SendMessage.ts

@@ -1039,7 +1039,7 @@ export default class MessageSender {
       myUuid || myNumber,
       contentMessage,
       timestamp,
-      ContentHint.SUPPLEMENTARY,
+      ContentHint.IMPLICIT,
       options
     );
   }
@@ -1067,7 +1067,7 @@ export default class MessageSender {
         myUuid || myNumber,
         contentMessage,
         Date.now(),
-        ContentHint.SUPPLEMENTARY,
+        ContentHint.IMPLICIT,
         options
       );
     }
@@ -1098,7 +1098,7 @@ export default class MessageSender {
         myUuid || myNumber,
         contentMessage,
         Date.now(),
-        ContentHint.SUPPLEMENTARY,
+        ContentHint.IMPLICIT,
         options
       );
     }
@@ -1128,7 +1128,7 @@ export default class MessageSender {
         myUuid || myNumber,
         contentMessage,
         Date.now(),
-        ContentHint.SUPPLEMENTARY,
+        ContentHint.IMPLICIT,
         options
       );
     }
@@ -1160,7 +1160,7 @@ export default class MessageSender {
         myUuid || myNumber,
         contentMessage,
         Date.now(),
-        ContentHint.SUPPLEMENTARY,
+        ContentHint.IMPLICIT,
         options
       );
     }
@@ -1196,7 +1196,7 @@ export default class MessageSender {
       myUuid || myNumber,
       contentMessage,
       Date.now(),
-      ContentHint.SUPPLEMENTARY,
+      ContentHint.IMPLICIT,
       options
     );
   }
@@ -1228,7 +1228,7 @@ export default class MessageSender {
       myUuid || myNumber,
       contentMessage,
       Date.now(),
-      ContentHint.SUPPLEMENTARY,
+      ContentHint.IMPLICIT,
       options
     );
   }
@@ -1266,7 +1266,7 @@ export default class MessageSender {
         myUuid || myNumber,
         contentMessage,
         Date.now(),
-        ContentHint.SUPPLEMENTARY,
+        ContentHint.DEFAULT,
         options
       );
     }
@@ -1306,7 +1306,7 @@ export default class MessageSender {
       myUuid || myNumber,
       contentMessage,
       Date.now(),
-      ContentHint.SUPPLEMENTARY,
+      ContentHint.IMPLICIT,
       options
     );
   }
@@ -1347,7 +1347,7 @@ export default class MessageSender {
       myUuid || myNumber,
       contentMessage,
       Date.now(),
-      ContentHint.SUPPLEMENTARY,
+      ContentHint.IMPLICIT,
       sendOptions
     );
   }
@@ -1395,7 +1395,7 @@ export default class MessageSender {
       myUuid || myNumber,
       contentMessage,
       Date.now(),
-      ContentHint.SUPPLEMENTARY,
+      ContentHint.IMPLICIT,
       options
     );
   }
@@ -1451,7 +1451,7 @@ export default class MessageSender {
         myUuid || myNumber,
         secondMessage,
         now,
-        ContentHint.SUPPLEMENTARY,
+        ContentHint.IMPLICIT,
         options
       );
     });
@@ -1484,7 +1484,7 @@ export default class MessageSender {
             }
           : {}),
       },
-      ContentHint.SUPPLEMENTARY,
+      ContentHint.IMPLICIT,
       undefined, // groupId
       sendOptions
     );
@@ -1509,7 +1509,7 @@ export default class MessageSender {
       finalTimestamp,
       recipients,
       contentMessage,
-      ContentHint.SUPPLEMENTARY,
+      ContentHint.DEFAULT,
       undefined, // groupId
       sendOptions
     );
@@ -1547,7 +1547,7 @@ export default class MessageSender {
       recipientUuid || recipientE164,
       contentMessage,
       Date.now(),
-      ContentHint.SUPPLEMENTARY,
+      ContentHint.IMPLICIT,
       options
     );
   }
@@ -1573,7 +1573,7 @@ export default class MessageSender {
       senderUuid || senderE164,
       contentMessage,
       Date.now(),
-      ContentHint.SUPPLEMENTARY,
+      ContentHint.IMPLICIT,
       options
     );
   }
@@ -1608,7 +1608,7 @@ export default class MessageSender {
       identifier,
       contentMessage,
       timestamp,
-      ContentHint.SUPPLEMENTARY,
+      ContentHint.IMPLICIT,
       options
     );
   }
@@ -1649,7 +1649,7 @@ export default class MessageSender {
           identifier,
           proto,
           timestamp,
-          ContentHint.SUPPLEMENTARY,
+          ContentHint.DEFAULT,
           options
         ).catch(logError('resetSession/sendToContact error:'));
       })
@@ -1702,7 +1702,7 @@ export default class MessageSender {
         flags:
           window.textsecure.protobuf.DataMessage.Flags.EXPIRATION_TIMER_UPDATE,
       },
-      ContentHint.SUPPLEMENTARY,
+      ContentHint.DEFAULT,
       undefined, // groupId
       options
     );
@@ -1725,7 +1725,7 @@ export default class MessageSender {
       Date.now(),
       [uuid],
       plaintext,
-      ContentHint.SUPPLEMENTARY,
+      ContentHint.IMPLICIT,
       undefined, // groupId
       options
     );
@@ -1864,7 +1864,7 @@ export default class MessageSender {
       groupIdentifiers,
       proto,
       Date.now(),
-      ContentHint.SUPPLEMENTARY,
+      ContentHint.DEFAULT,
       undefined, // only for GV2 ids
       options
     );
@@ -1911,7 +1911,7 @@ export default class MessageSender {
     } = window.textsecure.protobuf.UnidentifiedSenderMessage.Message;
     return this.sendMessage(
       attrs,
-      ContentHint.SUPPLEMENTARY,
+      ContentHint.DEFAULT,
       undefined, // only for GV2 ids
       options
     );

ts/util/retryPlaceholders.ts

@@ -11,6 +11,7 @@ const retryItemSchema = z
     receivedAt: z.number(),
     receivedAtCounter: z.number(),
     senderUuid: z.string(),
+    wasOpened: z.boolean().optional(),
   })
   .passthrough();
 export type RetryItemType = z.infer<typeof retryItemSchema>;
@@ -30,8 +31,8 @@ export function getItemId(conversationId: string, sentAt: number): string {
 const HOUR = 60 * 60 * 1000;
 export const STORAGE_KEY = 'retryPlaceholders';
 
-export function getOneHourAgo(): number {
+export function getDeltaIntoPast(delta?: number): number {
-  return Date.now() - HOUR;
+  return Date.now() - (delta || HOUR);
 }
 
 export class RetryPlaceholders {
@@ -41,7 +42,9 @@ export class RetryPlaceholders {
 
   private byMessage: ByMessageLookupType;
 
-  constructor() {
+  private retryReceiptLifespan: number;
+
+  constructor(options: { retryReceiptLifespan?: number } = {}) {
     if (!window.storage) {
       throw new Error(
         'RetryPlaceholders.constructor: window.storage not available!'
@@ -67,6 +70,7 @@ export class RetryPlaceholders {
     this.sortByExpiresAtAsc();
     this.byConversation = this.makeByConversationLookup();
     this.byMessage = this.makeByMessageLookup();
+    this.retryReceiptLifespan = options.retryReceiptLifespan || HOUR;
   }
 
   // Arranging local data for efficiency
@@ -128,7 +132,7 @@ export class RetryPlaceholders {
   }
 
   async getExpiredAndRemove(): Promise<Array<RetryItemType>> {
-    const expiration = getOneHourAgo();
+    const expiration = getDeltaIntoPast(this.retryReceiptLifespan);
     const max = this.items.length;
     const result: Array<RetryItemType> = [];
 
@@ -152,28 +156,24 @@ export class RetryPlaceholders {
     return result;
   }
 
-  async findByConversationAndRemove(
+  async findByConversationAndMarkOpened(conversationId: string): Promise<void> {
-    conversationId: string
+    let changed = 0;
-  ): Promise<Array<RetryItemType>> {
+    const items = this.byConversation[conversationId];
-    const result = this.byConversation[conversationId];
+    (items || []).forEach(item => {
-    if (!result) {
+      if (!item.wasOpened) {
-      return [];
+        changed += 1;
+        // eslint-disable-next-line no-param-reassign
+        item.wasOpened = true;
+      }
+    });
+
+    if (changed > 0) {
+      window.log.info(
+        `RetryPlaceholders.findByConversationAndMarkOpened: Updated ${changed} items for conversation ${conversationId}`
+      );
+
+      await this.save();
     }
-
-    const items = this.items.filter(
-      item => item.conversationId !== conversationId
-    );
-
-    window.log.info(
-      `RetryPlaceholders.findByConversationAndRemove: Found ${result.length} expired items`
-    );
-
-    this.items = items;
-    this.sortByExpiresAtAsc();
-    this.makeLookups();
-    await this.save();
-
-    return result;
   }
 
   async findByMessageAndRemove(

ts/util/sendToGroup.ts

@@ -16,6 +16,7 @@ import {
   padMessage,
   SenderCertificateMode,
 } from '../textsecure/OutgoingMessage';
+import { isEnabled } from '../RemoteConfig';
 
 import { isOlderThan } from './timestamp';
 import {
@@ -116,6 +117,7 @@ export async function sendContentMessageToGroup({
   const ourConversation = window.ConversationController.get(ourConversationId);
 
   if (
+    isEnabled('desktop.sendSenderKey') &&
     ourConversation?.get('capabilities')?.senderKey &&
     isGroupV2(conversation.attributes)
   ) {
@@ -199,8 +201,9 @@ export async function sendToGroupViaSenderKey(options: {
   }
 
   if (
+    contentHint !== ContentHint.DEFAULT &&
     contentHint !== ContentHint.RESENDABLE &&
-    contentHint !== ContentHint.SUPPLEMENTARY
+    contentHint !== ContentHint.IMPLICIT
   ) {
     throw new Error(
       `sendToGroupViaSenderKey/${logId}: Invalid contentHint ${contentHint}`
@@ -326,7 +329,7 @@ export async function sendToGroupViaSenderKey(options: {
     );
     await window.textsecure.messaging.sendSenderKeyDistributionMessage(
       {
-        contentHint: ContentHint.SUPPLEMENTARY,
+        contentHint: ContentHint.DEFAULT,
         distributionId,
         groupId,
         identifiers: newToMemberUuids,

ts/views/conversation_view.ts

@@ -2266,10 +2266,7 @@ Whisper.ConversationView = Whisper.View.extend({
 
     const { retryPlaceholders } = window.Signal.Services;
     if (retryPlaceholders) {
-      const placeholders = await retryPlaceholders.findByConversationAndRemove(
+      await retryPlaceholders.findByConversationAndMarkOpened(model.id);
-        model.id
-      );
-      window.log.info(`onOpened: Found ${placeholders.length} placeholders`);
     }
 
     this.loadNewestMessages();