diff --git a/packages/frontend/src/data/models/message/model.ts b/packages/frontend/src/data/models/message/model.ts
index cc7ddcb0cd..4831f153c7 100644
--- a/packages/frontend/src/data/models/message/model.ts
+++ b/packages/frontend/src/data/models/message/model.ts
@@ -116,6 +116,13 @@ export default class Message extends Model {
 
   @attr() sendError?: string;
 
+  /**
+   * When a user comes online, they dispatch a bunch of pings to their contacts.
+   * If any of those contacts have queue messages (designated by this boolean)
+   * the messages will automatically be sent to the user who jest came online
+   * */
+  @attr() queueForResend?: boolean;
+
   @belongsTo('identity', { async: false }) sender?: Identity;
 
   // @belongsTo('message', { async: false, inverse: 'deliveryConfirmations' }) confirmationFor?: Message;
diff --git a/packages/frontend/src/services/messages/auto-responder.ts b/packages/frontend/src/services/messages/auto-responder.ts
index d4afd0902c..f3d4328113 100644
--- a/packages/frontend/src/services/messages/auto-responder.ts
+++ b/packages/frontend/src/services/messages/auto-responder.ts
@@ -1,9 +1,11 @@
 import Service from '@ember/service';
 import { service } from '@ember-decorators/service';
+import StoreService from 'ember-data/store';
 
 import MessageDispatcher from 'emberclear/src/services/messages/dispatcher';
 import MessageFactory from 'emberclear/src/services/messages/factory';
 import Message from 'emberclear/src/data/models/message/model';
+import Identity from 'emberclear/src/data/models/identity/model';
 
 /**
  * Nothing here should be blocking, as these responses should not matter
@@ -14,6 +16,7 @@ import Message from 'emberclear/src/data/models/message/model';
 export default class MessageAutoResponder extends Service {
   @service('messages/dispatcher') dispatcher!: MessageDispatcher;
   @service('messages/factory') factory!: MessageFactory;
+  @service store!: StoreService;
 
   async messageReceived(respondToMessage: Message) {
     const sender = await respondToMessage.sender;
@@ -21,6 +24,17 @@ export default class MessageAutoResponder extends Service {
 
     this.dispatcher.sendToUser.perform(response, sender);
   }
+
+  async cameOnline(identity: Identity) {
+    const pendingMessages = await this.store.query('message', {
+      queueForResend: true,
+      to: identity.uid,
+    });
+
+    pendingMessages.forEach((message: Message) => {
+      this.dispatcher.sendToUser.perform(message, identity);
+    });
+  }
 }
 
 // DO NOT DELETE: this is how TypeScript knows how to look up your services.
diff --git a/packages/frontend/src/services/messages/dispatcher.ts b/packages/frontend/src/services/messages/dispatcher.ts
index 0604cb5b15..e9d3639391 100644
--- a/packages/frontend/src/services/messages/dispatcher.ts
+++ b/packages/frontend/src/services/messages/dispatcher.ts
@@ -33,7 +33,14 @@ export default class MessageDispatcher extends Service {
     this.sendTo(message, to);
   }
 
+  // there needs to be a polymorphic relationship in order for this to work
+  // sendMessage(message: Message) {
+  //   return sendTo(message, message.to);
+  // }
+
   async sendTo(message: Message, to: Identity | Channel) {
+    message.set('queueForResend', false);
+
     if (to instanceof Identity) {
       if (to.id === 'me') return;
 
diff --git a/packages/frontend/src/services/messages/handler/service.ts b/packages/frontend/src/services/messages/handler/service.ts
index dc3f379b1d..b7183d8f19 100644
--- a/packages/frontend/src/services/messages/handler/service.ts
+++ b/packages/frontend/src/services/messages/handler/service.ts
@@ -110,6 +110,7 @@ export default class ReceivedMessageHandler extends Service {
     const sender = await this.findOrCreateSender(senderInfo);
 
     this.statusManager.markOnline(sender);
+    this.autoResponder.cameOnline(sender);
 
     const message = this.store.createRecord('message', {
       id,
diff --git a/packages/frontend/src/services/toast.ts b/packages/frontend/src/services/toast.ts
index a5b8d8950a..e079214b3b 100644
--- a/packages/frontend/src/services/toast.ts
+++ b/packages/frontend/src/services/toast.ts
@@ -32,7 +32,7 @@ export default class Toast extends Service {
       ...options,
       message: message || 'status',
       type: status,
-      cssClasses: `notification ${status} p-xs has-shadow height-tall`,
+      cssClasses: `notification ${status} is-${status} p-xs has-shadow height-tall`,
     });
   }
 }
diff --git a/packages/frontend/src/ui/components/chat-history/message/delivery-confirmations/component.ts b/packages/frontend/src/ui/components/chat-history/message/delivery-confirmations/component.ts
index 5fee9f5983..40c5ab6e9d 100644
--- a/packages/frontend/src/ui/components/chat-history/message/delivery-confirmations/component.ts
+++ b/packages/frontend/src/ui/components/chat-history/message/delivery-confirmations/component.ts
@@ -77,4 +77,13 @@ export default class DeliveryConfirmation extends Component<IArgs> {
 
     yield message.destroyRecord();
   }
+
+  @dropTask
+  *resendAutomatically(this: DeliveryConfirmation) {
+    const { message } = this.args;
+
+    message.set('queueForResend', true);
+
+    yield message.save();
+  }
 }
diff --git a/packages/frontend/src/ui/components/chat-history/message/delivery-confirmations/template.hbs b/packages/frontend/src/ui/components/chat-history/message/delivery-confirmations/template.hbs
index 5a82dade9f..0b3d15dd07 100644
--- a/packages/frontend/src/ui/components/chat-history/message/delivery-confirmations/template.hbs
+++ b/packages/frontend/src/ui/components/chat-history/message/delivery-confirmations/template.hbs
@@ -15,6 +15,14 @@
         {{#if this.resend.isIdle}}
           <a {{action (perform this.resend)}}>{{t 'buttons.resend'}}</a>
         {{/if}}
+        |
+        {{#if this.resendAutomatically.isIdle}}
+          {{#if @message.queueForResend}}
+            {{t 'models.message.autosendPending'}}
+          {{else}}
+            <a {{action (perform this.resendAutomatically)}}>{{t 'buttons.resendAutomatically'}}</a>
+          {{/if}}
+        {{/if}}
 
         {{fa-icon 'exclamation-circle'}}
 
diff --git a/packages/frontend/translations/en-us.yaml b/packages/frontend/translations/en-us.yaml
index 9e86eefb85..d185c5ab1f 100644
--- a/packages/frontend/translations/en-us.yaml
+++ b/packages/frontend/translations/en-us.yaml
@@ -27,6 +27,7 @@ connection:
 buttons:
   delete: delete
   resend: resend
+  resendAutomatically: resend automatically
   save: Save
   next: Next
   back: Back
@@ -89,6 +90,7 @@ models:
     publicKey: Public Key
 
   message:
+    autosendPending: autosend pending
     errors:
       timeout: 'Sending timed out.'