diff --git a/spec/stores/draft-store-spec.es6 b/spec/stores/draft-store-spec.es6
index 6a3809efd..b82b749d2 100644
--- a/spec/stores/draft-store-spec.es6
+++ b/spec/stores/draft-store-spec.es6
@@ -412,7 +412,7 @@ xdescribe('DraftStore', function draftStore() {
     it("resets the sending state if there's an error", () => {
       spyOn(NylasEnv, "isMainWindow").andReturn(false);
       DraftStore._draftsSending[this.draft.clientId] = true;
-      Actions.sendDraftFailed({errorMessage: "boohoo", draftClientId: this.draft.clientId});
+      Actions.draftDeliveryFailed({errorMessage: "boohoo", draftClientId: this.draft.clientId});
       expect(DraftStore.isSendingDraft(this.draft.clientId)).toBe(false);
       expect(DraftStore.trigger).toHaveBeenCalledWith(this.draft.clientId);
     });
@@ -423,7 +423,7 @@ xdescribe('DraftStore', function draftStore() {
       spyOn(remote.dialog, "showMessageBox");
       spyOn(Actions, "composePopoutDraft");
       DraftStore._draftsSending[this.draft.clientId] = true;
-      Actions.sendDraftFailed({threadId: 't1', errorMessage: "boohoo", draftClientId: this.draft.clientId});
+      Actions.draftDeliveryFailed({threadId: 't1', errorMessage: "boohoo", draftClientId: this.draft.clientId});
       advanceClock(400);
       expect(DraftStore.isSendingDraft(this.draft.clientId)).toBe(false);
       expect(DraftStore.trigger).toHaveBeenCalledWith(this.draft.clientId);
@@ -438,7 +438,7 @@ xdescribe('DraftStore', function draftStore() {
       spyOn(FocusedContentStore, "focused").andReturn({id: "t1"});
       spyOn(Actions, "composePopoutDraft");
       DraftStore._draftsSending[this.draft.clientId] = true;
-      Actions.sendDraftFailed({threadId: 't2', errorMessage: "boohoo", draftClientId: this.draft.clientId});
+      Actions.draftDeliveryFailed({threadId: 't2', errorMessage: "boohoo", draftClientId: this.draft.clientId});
       advanceClock(400);
       expect(Actions.composePopoutDraft).toHaveBeenCalled();
       const call = Actions.composePopoutDraft.calls[0];
@@ -451,7 +451,7 @@ xdescribe('DraftStore', function draftStore() {
       spyOn(Actions, "composePopoutDraft");
       DraftStore._draftsSending[this.draft.clientId] = true;
       spyOn(FocusedContentStore, "focused").andReturn(null);
-      Actions.sendDraftFailed({errorMessage: "boohoo", draftClientId: this.draft.clientId});
+      Actions.draftDeliveryFailed({errorMessage: "boohoo", draftClientId: this.draft.clientId});
       advanceClock(400);
       expect(Actions.composePopoutDraft).toHaveBeenCalled();
       const call = Actions.composePopoutDraft.calls[0];
diff --git a/spec/stores/file-upload-store-spec.coffee b/spec/stores/file-upload-store-spec.coffee
index c82ff698d..4bbb233c3 100644
--- a/spec/stores/file-upload-store-spec.coffee
+++ b/spec/stores/file-upload-store-spec.coffee
@@ -133,7 +133,7 @@ xdescribe 'FileUploadStore', ->
   describe "when a draft is sent", ->
     it "should delete its uploads directory", ->
       spyOn(FileUploadStore, '_deleteUploadsForClientId')
-      Actions.sendDraftSuccess({messageClientId: '123'})
+      Actions.ensureMessageInSentSuccess({messageClientId: '123'})
       expect(FileUploadStore._deleteUploadsForClientId).toHaveBeenCalledWith('123')
 
   describe '_getFileStats', ->
diff --git a/spec/tasks/send-draft-task-spec.es6 b/spec/tasks/send-draft-task-spec.es6
index b88f3e066..fea2bc8a6 100644
--- a/spec/tasks/send-draft-task-spec.es6
+++ b/spec/tasks/send-draft-task-spec.es6
@@ -93,7 +93,7 @@ xdescribe('SendDraftTask', function sendDraftTask() {
       spyOn(DBt, 'unpersistModel').andReturn(Promise.resolve());
       spyOn(DBt, 'persistModel').andReturn(Promise.resolve());
       spyOn(SoundRegistry, "playSound");
-      spyOn(Actions, "sendDraftSuccess");
+      spyOn(Actions, "draftDeliverySucceeded");
     });
 
     // The tests below are invoked twice, once with a new this.draft and one with a
@@ -165,7 +165,7 @@ xdescribe('SendDraftTask', function sendDraftTask() {
 
       it("should notify the draft was sent", () => {
         waitsForPromise(() => this.task.performRemote().then(() => {
-          const args = Actions.sendDraftSuccess.calls[0].args[0];
+          const args = Actions.draftDeliverySucceeded.calls[0].args[0];
           expect(args.message instanceof Message).toBe(true)
           expect(args.messageClientId).toBe(this.draft.clientId)
         }));
@@ -203,7 +203,7 @@ xdescribe('SendDraftTask', function sendDraftTask() {
 
       describe("when there are errors", () => {
         beforeEach(() => {
-          spyOn(Actions, 'sendDraftFailed');
+          spyOn(Actions, 'draftDeliveryFailed');
           jasmine.unspy(NylasAPIRequest.prototype, "run");
         });
 
@@ -219,7 +219,7 @@ xdescribe('SendDraftTask', function sendDraftTask() {
           waitsForPromise(() => this.task.performRemote().then((status) => {
             expect(status[0]).toBe(Task.Status.Failed);
             expect(status[1]).toBe(thrownError);
-            expect(Actions.sendDraftFailed).toHaveBeenCalled();
+            expect(Actions.draftDeliveryFailed).toHaveBeenCalled();
             expect(NylasEnv.reportError).toHaveBeenCalled();
           }));
         });
@@ -284,7 +284,7 @@ xdescribe('SendDraftTask', function sendDraftTask() {
           waitsForPromise(() => this.task.performRemote().then((status) => {
             expect(status[0]).toBe(Task.Status.Failed);
             expect(status[1]).toBe(thrownError);
-            expect(Actions.sendDraftFailed).toHaveBeenCalled();
+            expect(Actions.draftDeliveryFailed).toHaveBeenCalled();
           }));
         });
 
@@ -296,7 +296,7 @@ xdescribe('SendDraftTask', function sendDraftTask() {
           waitsForPromise(() => this.task.performRemote().then((status) => {
             expect(status[0]).toBe(Task.Status.Failed);
             expect(status[1]).toBe(thrownError);
-            expect(Actions.sendDraftFailed).toHaveBeenCalled();
+            expect(Actions.draftDeliveryFailed).toHaveBeenCalled();
           }));
         });
 
@@ -325,9 +325,9 @@ xdescribe('SendDraftTask', function sendDraftTask() {
           waitsForPromise(() => this.task.performRemote().then((status) => {
             expect(status[0]).toBe(Task.Status.Failed);
             expect(status[1]).toBe(thrownError);
-            expect(Actions.sendDraftFailed).toHaveBeenCalled();
+            expect(Actions.draftDeliveryFailed).toHaveBeenCalled();
 
-            const msg = Actions.sendDraftFailed.calls[0].args[0].errorMessage;
+            const msg = Actions.draftDeliveryFailed.calls[0].args[0].errorMessage;
             expect(withoutWhitespace(msg)).toEqual(withoutWhitespace(expectedMessage));
           }));
         });
@@ -349,9 +349,9 @@ xdescribe('SendDraftTask', function sendDraftTask() {
           waitsForPromise(() => this.task.performRemote().then((status) => {
             expect(status[0]).toBe(Task.Status.Failed);
             expect(status[1]).toBe(thrownError);
-            expect(Actions.sendDraftFailed).toHaveBeenCalled();
+            expect(Actions.draftDeliveryFailed).toHaveBeenCalled();
 
-            const msg = Actions.sendDraftFailed.calls[0].args[0].errorMessage;
+            const msg = Actions.draftDeliveryFailed.calls[0].args[0].errorMessage;
             expect(withoutWhitespace(msg)).toEqual(withoutWhitespace(expectedMessage));
           }));
         });
@@ -509,7 +509,7 @@ xdescribe('SendDraftTask', function sendDraftTask() {
     });
   });
 
-  describe("usingMultiSend", () => {
+  describe("hasCustomBodyPerRecipient", () => {
     beforeEach(() => {
       this.task = new SendDraftTask('client-id');
       this.task.allowMultiSend = true;
@@ -545,13 +545,13 @@ xdescribe('SendDraftTask', function sendDraftTask() {
 
     it("should return false if the provider is eas", () => {
       this.applySpies({"AccountStore.accountForId": "eas"})
-      expect(this.task.usingMultiSend()).toBe(false);
+      expect(this.task.hasCustomBodyPerRecipient()).toBe(false);
     });
 
     it("should return false if allowMultiSend is false", () => {
       this.applySpies();
       this.task.allowMultiSend = false;
-      expect(this.task.usingMultiSend()).toBe(false);
+      expect(this.task.hasCustomBodyPerRecipient()).toBe(false);
     });
 
     it("should return false if the open-tracking id is null", () => {
@@ -559,7 +559,7 @@ xdescribe('SendDraftTask', function sendDraftTask() {
         return name === "open-tracking" ? null : name;
       };
       this.applySpies({"NylasEnv.packages.pluginIdFor": fake});
-      expect(this.task.usingMultiSend()).toBe(false);
+      expect(this.task.hasCustomBodyPerRecipient()).toBe(false);
     });
 
     it("should return false if the link-tracking id is null", () => {
@@ -567,36 +567,36 @@ xdescribe('SendDraftTask', function sendDraftTask() {
         return name === "link-tracking" ? null : name;
       };
       this.applySpies({"NylasEnv.packages.pluginIdFor": fake});
-      expect(this.task.usingMultiSend()).toBe(false);
+      expect(this.task.hasCustomBodyPerRecipient()).toBe(false);
     });
 
     it("should return false if neither open-tracking nor link-tracking is on", () => {
       this.applySpies();
       this.task.draft.applyPluginMetadata('open-tracking', false);
       this.task.draft.applyPluginMetadata('link-tracking', false);
-      expect(this.task.usingMultiSend()).toBe(false);
+      expect(this.task.hasCustomBodyPerRecipient()).toBe(false);
     });
 
     it("should return true if only open-tracking is on", () => {
       this.applySpies();
       this.task.draft.applyPluginMetadata('link-tracking', false);
-      expect(this.task.usingMultiSend()).toBe(true);
+      expect(this.task.hasCustomBodyPerRecipient()).toBe(true);
     });
 
     it("should return true if only link-tracking is on", () => {
       this.applySpies();
       this.task.draft.applyPluginMetadata('open-tracking', false);
-      expect(this.task.usingMultiSend()).toBe(true);
+      expect(this.task.hasCustomBodyPerRecipient()).toBe(true);
     });
 
     it("should return false if there are too many participants", () => {
       this.applySpies({"draft.participants": 15});
-      expect(this.task.usingMultiSend()).toBe(false);
+      expect(this.task.hasCustomBodyPerRecipient()).toBe(false);
     });
 
     it("should return true otherwise", () => {
       this.applySpies();
-      expect(this.task.usingMultiSend()).toBe(true);
+      expect(this.task.hasCustomBodyPerRecipient()).toBe(true);
     });
   });
 });
diff --git a/src/K2 b/src/K2
index ab9eeaafc..09f19d1ad 160000
--- a/src/K2
+++ b/src/K2
@@ -1 +1 @@
-Subproject commit ab9eeaafce307976e2639cfc089ff534a7ba2082
+Subproject commit 09f19d1adfec03c99fae0b4a1610b6c51e47f491
diff --git a/src/flux/actions.es6 b/src/flux/actions.es6
index af8f867c7..2d12476f1 100644
--- a/src/flux/actions.es6
+++ b/src/flux/actions.es6
@@ -423,8 +423,11 @@ class Actions {
 
   Recieves the clientId of the message that was sent
   */
-  static sendDraftSuccess = ActionScopeGlobal;
-  static sendDraftFailed = ActionScopeGlobal;
+  static draftDeliverySucceeded = ActionScopeGlobal;
+  static draftDeliveryFailed = ActionScopeGlobal;
+
+  static ensureMessageInSentSuccess = ActionScopeGlobal;
+  static ensureMessageInSentFailed = ActionScopeGlobal;
 
   static sendManyDrafts = ActionScopeWindow;
   static ensureDraftSynced = ActionScopeWindow;
diff --git a/src/flux/stores/draft-store.es6 b/src/flux/stores/draft-store.es6
index 7f73a39cd..cf9c9869a 100644
--- a/src/flux/stores/draft-store.es6
+++ b/src/flux/stores/draft-store.es6
@@ -41,8 +41,8 @@ class DraftStore extends NylasStore {
     this.listenTo(Actions.composePopoutDraft, this._onPopoutDraftClientId);
     this.listenTo(Actions.composeNewBlankDraft, this._onPopoutBlankDraft);
     this.listenTo(Actions.composeNewDraftToRecipient, this._onPopoutNewDraftToRecipient);
-    this.listenTo(Actions.sendDraftFailed, this._onSendDraftFailed);
-    this.listenTo(Actions.sendDraftSuccess, this._onSendDraftSuccess);
+    this.listenTo(Actions.draftDeliveryFailed, this._onSendDraftFailed);
+    this.listenTo(Actions.draftDeliverySucceeded, this._onSendDraftSuccess);
     this.listenTo(Actions.didCancelSendAction, this._onDidCancelSendAction);
     this.listenTo(Actions.sendQuickReply, this._onSendQuickReply);
 
diff --git a/src/flux/stores/file-upload-store.es6 b/src/flux/stores/file-upload-store.es6
index d4e075275..3a65add4f 100644
--- a/src/flux/stores/file-upload-store.es6
+++ b/src/flux/stores/file-upload-store.es6
@@ -49,7 +49,7 @@ class FileUploadStore extends NylasStore {
 
     mkdirp.sync(UPLOAD_DIR);
     if (NylasEnv.isMainWindow() || NylasEnv.inSpecMode()) {
-      this.listenTo(Actions.sendDraftSuccess, ({messageClientId}) => {
+      this.listenTo(Actions.ensureMessageInSentSuccess, ({messageClientId}) => {
         this._deleteUploadsForClientId(messageClientId);
       });
     }
diff --git a/src/flux/syncback-task-api-request.es6 b/src/flux/syncback-task-api-request.es6
index 8a9165eee..70faf5468 100644
--- a/src/flux/syncback-task-api-request.es6
+++ b/src/flux/syncback-task-api-request.es6
@@ -41,7 +41,7 @@ class SyncbackTaskAPIRequest {
                 message: failed.error.message,
                 data: failed.error.data,
               },
-              statusCode: failed.error.statusCode,
+              statusCode: failed.error.statusCode || 500,
             })
             reject(error)
           } else if (succeeded) {
diff --git a/src/flux/tasks/reconcile-multi-send-task.es6 b/src/flux/tasks/ensure-message-in-sent-folder-task.es6
similarity index 64%
rename from src/flux/tasks/reconcile-multi-send-task.es6
rename to src/flux/tasks/ensure-message-in-sent-folder-task.es6
index 8f845f4e9..6e20a7d73 100644
--- a/src/flux/tasks/reconcile-multi-send-task.es6
+++ b/src/flux/tasks/ensure-message-in-sent-folder-task.es6
@@ -1,14 +1,16 @@
 import Task from './task';
 import {APIError} from '../errors';
+import Actions from '../actions';
 import NylasAPI from '../nylas-api';
 import SyncbackTaskAPIRequest from '../syncback-task-api-request';
 import SendDraftTask from './send-draft-task';
 
 
-export default class ReconcileMultiSendTask extends Task {
+export default class EnsureMessageInSentFolderTask extends Task {
   constructor(opts = {}) {
     super(opts);
     this.message = opts.message;
+    this.sentPerRecipient = opts.sentPerRecipient;
   }
 
   isDependentOnTask(other) {
@@ -27,18 +29,24 @@ export default class ReconcileMultiSendTask extends Task {
     return new SyncbackTaskAPIRequest({
       api: NylasAPI,
       options: {
-        timeout: 1000 * 60 * 5, // We cannot hang up a send - won't know if it sent
-        method: "DELETE",
-        path: `/send-multiple/${this.message.id}`,
+        path: `/ensure-message-in-sent-folder/${this.message.id}`,
+        method: "POST",
+        body: {
+          sentPerRecipient: this.sentPerRecipient,
+        },
         accountId: this.message.accountId,
       },
     })
     .run()
-    .thenReturn(Task.Status.Success)
+    .then(() => {
+      Actions.ensureMessageInSentSuccess({messageClientId: this.message.clientId})
+      return Task.Status.Success
+    })
     .catch((err) => {
-      const errorMessage = `We had trouble saving your message, "${this.message.subject}", to your Sent folder.\n\n${err.message}`;
+      const errorMessage = `Your message successfully sent; however, we had trouble saving your message, "${this.message.subject}", to your Sent folder.\n\n${err.message}`;
+      Actions.ensureMessageInSentFailed()
       if (err instanceof APIError) {
-        if (SyncbackTaskAPIRequest.PermanentErrorCodes.includes(err.statusCode)) {
+        if (NylasAPI.PermanentErrorCodes.includes(err.statusCode)) {
           NylasEnv.showErrorDialog(errorMessage, {showInMainWindow: true, detail: err.stack});
           return Promise.resolve([Task.Status.Failed, err]);
         }
diff --git a/src/flux/tasks/send-draft-task.es6 b/src/flux/tasks/send-draft-task.es6
index 88660bb6f..09fb51597 100644
--- a/src/flux/tasks/send-draft-task.es6
+++ b/src/flux/tasks/send-draft-task.es6
@@ -11,8 +11,7 @@ import DatabaseStore from '../stores/database-store';
 import AccountStore from '../stores/account-store';
 import BaseDraftTask from './base-draft-task';
 import SyncbackMetadataTask from './syncback-metadata-task';
-import ReconcileMultiSendTask from './reconcile-multi-send-task';
-
+import EnsureMessageInSentFolderTask from './ensure-message-in-sent-folder-task';
 
 const OPEN_TRACKING_ID = NylasEnv.packages.pluginIdFor('open-tracking')
 const LINK_TRACKING_ID = NylasEnv.packages.pluginIdFor('link-tracking')
@@ -38,6 +37,7 @@ export default class SendDraftTask extends BaseDraftTask {
     return this.refreshDraftReference()
     .then(this.assertDraftValidity)
     .then(this.sendMessage)
+    .then(this.ensureInSentFolder)
     .then(this.updatePluginMetadata)
     .then(this.onSuccess)
     .catch(this.onError);
@@ -58,7 +58,7 @@ export default class SendDraftTask extends BaseDraftTask {
     return Promise.resolve();
   }
 
-  usingMultiSend = () => {
+  hasCustomBodyPerRecipient = () => {
     if (!this.allowMultiSend) {
       return false;
     }
@@ -73,17 +73,29 @@ export default class SendDraftTask extends BaseDraftTask {
     if (!pluginsAvailable) {
       return false;
     }
-    const pluginsInUse = (this.draft.metadataForPluginId(OPEN_TRACKING_ID) || this.draft.metadataForPluginId(LINK_TRACKING_ID));
+    const pluginsInUse = (this.draft.metadataForPluginId(OPEN_TRACKING_ID) || this.draft.metadataForPluginId(LINK_TRACKING_ID)) || false;
     const providerCompatible = (AccountStore.accountForId(this.draft.accountId).provider !== "eas");
     return pluginsInUse && providerCompatible;
   }
 
-  sendMessage = () => {
-    return this.usingMultiSend() ? this.sendWithMultipleBodies() : this.sendWithSingleBody();
+  sendMessage = async () => {
+    if (this.hasCustomBodyPerRecipient()) {
+      await this._sendPerRecipient();
+    } else {
+      await this._sendWithSingleBody()
+    }
   }
 
-  sendWithSingleBody = () => {
-    return new SyncbackTaskAPIRequest({
+  ensureInSentFolder = () => {
+    const t = new EnsureMessageInSentFolderTask({
+      message: this.message,
+      sentPerRecipient: this.hasCustomBodyPerRecipient(),
+    })
+    Actions.queueTask(t)
+  }
+
+  _sendWithSingleBody = async () => {
+    const task = new SyncbackTaskAPIRequest({
       api: NylasAPI,
       options: {
         path: "/send",
@@ -95,17 +107,15 @@ export default class SendDraftTask extends BaseDraftTask {
         requestId: this.draft.clientId,
       },
     })
-    .run()
-    .then((responseJSON) => {
-      return this.createMessageFromResponse(responseJSON)
-    })
+    const responseJSON = await task.run();
+    await this._createMessageFromResponse(responseJSON)
   }
 
-  sendWithMultipleBodies = () => {
-    return new SyncbackTaskAPIRequest({
+  _sendPerRecipient = async () => {
+    const task = new SyncbackTaskAPIRequest({
       api: NylasAPI,
       options: {
-        path: "/send-multiple",
+        path: "/send-per-recipient",
         accountId: this.draft.accountId,
         method: 'POST',
         body: {
@@ -116,16 +126,8 @@ export default class SendDraftTask extends BaseDraftTask {
         timeout: 1000 * 60 * 5, // We cannot hang up a send - won't know if it sent
       },
     })
-    .run()
-    .then((responseJSON) => {
-      return this.createMessageFromResponse(responseJSON);
-    })
-    .then(() => {
-      const t = new ReconcileMultiSendTask({
-        message: this.message,
-      });
-      Actions.queueTask(t);
-    })
+    const responseJSON = await task.run();
+    await this._createMessageFromResponse(responseJSON);
   }
 
   updatePluginMetadata = () => {
@@ -138,7 +140,7 @@ export default class SendDraftTask extends BaseDraftTask {
     return Promise.resolve();
   }
 
-  createMessageFromResponse = (responseJSON) => {
+  _createMessageFromResponse = (responseJSON) => {
     const {failedRecipients, message} = responseJSON
     if (failedRecipients && failedRecipients.length > 0) {
       const errorMessage = `We had trouble sending this message to all recipients. ${failedRecipients} may not have received this email.`;
@@ -160,7 +162,7 @@ export default class SendDraftTask extends BaseDraftTask {
 
   onSuccess = () => {
     Actions.recordUserEvent("Draft Sent")
-    Actions.sendDraftSuccess({message: this.message, messageClientId: this.message.clientId, draftClientId: this.draft.clientId});
+    Actions.draftDeliverySucceeded({message: this.message, messageClientId: this.message.clientId, draftClientId: this.draft.clientId});
     // TODO we shouldn't need to do this anymore
     NylasAPIHelpers.makeDraftDeletionRequest(this.draft);
 
@@ -197,7 +199,7 @@ export default class SendDraftTask extends BaseDraftTask {
     }
 
     if (this.emitError && !(err instanceof RequestEnsureOnceError)) {
-      Actions.sendDraftFailed({
+      Actions.draftDeliveryFailed({
         threadId: this.draft.threadId,
         draftClientId: this.draft.clientId,
         errorMessage: message,
diff --git a/src/global/nylas-exports.es6 b/src/global/nylas-exports.es6
index a4f6798da..81a518e79 100644
--- a/src/global/nylas-exports.es6
+++ b/src/global/nylas-exports.es6
@@ -125,7 +125,7 @@ lazyLoadAndRegisterTask(`SyncbackCategoryTask`, 'syncback-category-task');
 lazyLoadAndRegisterTask(`SyncbackMetadataTask`, 'syncback-metadata-task');
 lazyLoadAndRegisterTask(`PerformSendActionTask`, 'perform-send-action-task');
 lazyLoadAndRegisterTask(`ReprocessMailRulesTask`, 'reprocess-mail-rules-task');
-lazyLoadAndRegisterTask(`ReconcileMultiSendTask`, 'reconcile-multi-send-task');
+lazyLoadAndRegisterTask(`EnsureMessageInSentFolderTask`, 'ensure-message-in-sent-folder-task');
 
 // Stores
 // These need to be required immediately since some Stores are