diff --git a/app/javascript/dashboard/api/integrations/openapi.js b/app/javascript/dashboard/api/integrations/openapi.js
index 88507bf81..641cfcfbd 100644
--- a/app/javascript/dashboard/api/integrations/openapi.js
+++ b/app/javascript/dashboard/api/integrations/openapi.js
@@ -7,14 +7,22 @@ class OpenAIAPI extends ApiClient {
     super('integrations', { accountScoped: true });
   }
 
-  processEvent({ name = 'rephrase', content, tone, hookId }) {
+  processEvent({ type = 'rephrase', content, tone, conversationId, hookId }) {
+    let data = {
+      tone,
+      content,
+    };
+
+    if (type === 'reply_suggestion' || type === 'summarize') {
+      data = {
+        conversation_display_id: conversationId,
+      };
+    }
+
     return axios.post(`${this.url}/hooks/${hookId}/process_event`, {
       event: {
-        name: name,
-        data: {
-          tone,
-          content,
-        },
+        name: type,
+        data,
       },
     });
   }
diff --git a/app/javascript/dashboard/assets/scss/_foundation-settings.scss b/app/javascript/dashboard/assets/scss/_foundation-settings.scss
index 28defb4fd..a6e0b1aa3 100644
--- a/app/javascript/dashboard/assets/scss/_foundation-settings.scss
+++ b/app/javascript/dashboard/assets/scss/_foundation-settings.scss
@@ -254,7 +254,7 @@ $button-sizes: (tiny: var(--font-size-micro),
   default: var(--font-size-small),
   large: var(--font-size-medium));
 $button-palette: $foundation-palette;
-$button-opacity-disabled: 0.25;
+$button-opacity-disabled: 0.4;
 $button-background-hover-lightness: -20%;
 $button-hollow-hover-lightness: -50%;
 $button-transition: background-color 0.25s ease-out,
diff --git a/app/javascript/dashboard/components/ui/WootButton.vue b/app/javascript/dashboard/components/ui/WootButton.vue
index 1571109c8..254f12d2f 100644
--- a/app/javascript/dashboard/components/ui/WootButton.vue
+++ b/app/javascript/dashboard/components/ui/WootButton.vue
@@ -6,7 +6,11 @@
     :disabled="isDisabled || isLoading"
     @click="handleClick"
   >
-    <spinner v-if="isLoading" size="small" />
+    <spinner
+      v-if="isLoading"
+      size="small"
+      :color-scheme="showDarkSpinner ? 'dark' : ''"
+    />
     <emoji-or-icon
       v-else-if="icon || emoji"
       class="icon"
@@ -108,6 +112,14 @@ export default {
           return 16;
       }
     },
+    showDarkSpinner() {
+      return (
+        this.colorScheme === 'secondary' ||
+        this.variant === 'clear' ||
+        this.variant === 'link' ||
+        this.variant === 'hollow'
+      );
+    },
   },
   methods: {
     handleClick(evt) {
diff --git a/app/javascript/dashboard/components/widgets/AIAssistanceButton.vue b/app/javascript/dashboard/components/widgets/AIAssistanceButton.vue
index 7c58f2aeb..98629edf3 100644
--- a/app/javascript/dashboard/components/widgets/AIAssistanceButton.vue
+++ b/app/javascript/dashboard/components/widgets/AIAssistanceButton.vue
@@ -1,45 +1,70 @@
 <template>
   <div v-if="isAIIntegrationEnabled" class="position-relative">
-    <woot-button
-      v-tooltip.top-end="$t('INTEGRATION_SETTINGS.OPEN_AI.TITLE')"
-      icon="wand"
-      color-scheme="secondary"
-      variant="smooth"
-      size="small"
-      @click="toggleDropdown"
-    />
-    <div
-      v-if="showDropdown"
-      v-on-clickaway="closeDropdown"
-      class="dropdown-pane dropdown-pane--open ai-modal"
-    >
-      <h4 class="sub-block-title margin-top-1">
-        {{ $t('INTEGRATION_SETTINGS.OPEN_AI.TITLE') }}
-      </h4>
-      <p>
-        {{ $t('INTEGRATION_SETTINGS.OPEN_AI.SUBTITLE') }}
-      </p>
-      <label>
-        {{ $t('INTEGRATION_SETTINGS.OPEN_AI.TONE.TITLE') }}
-      </label>
-      <div class="tone__item">
-        <select v-model="activeTone" class="status--filter small">
-          <option v-for="tone in tones" :key="tone.key" :value="tone.key">
-            {{ tone.value }}
-          </option>
-        </select>
-      </div>
-      <div class="modal-footer flex-container align-right">
-        <woot-button variant="clear" size="small" @click="closeDropdown">
-          {{ $t('INTEGRATION_SETTINGS.OPEN_AI.BUTTONS.CANCEL') }}
-        </woot-button>
-        <woot-button
-          :is-loading="isGenerating"
-          size="small"
-          @click="processText"
-        >
-          {{ buttonText }}
-        </woot-button>
+    <div v-if="!message">
+      <woot-button
+        v-if="isPrivateNote"
+        v-tooltip.top-end="$t('INTEGRATION_SETTINGS.OPEN_AI.SUMMARY_TITLE')"
+        icon="book-pulse"
+        color-scheme="secondary"
+        variant="smooth"
+        size="small"
+        :is-loading="uiFlags.summarize"
+        @click="processEvent('summarize')"
+      />
+      <woot-button
+        v-else
+        v-tooltip.top-end="$t('INTEGRATION_SETTINGS.OPEN_AI.REPLY_TITLE')"
+        icon="wand"
+        color-scheme="secondary"
+        variant="smooth"
+        size="small"
+        :is-loading="uiFlags.reply_suggestion"
+        @click="processEvent('reply_suggestion')"
+      />
+    </div>
+
+    <div v-else>
+      <woot-button
+        v-tooltip.top-end="$t('INTEGRATION_SETTINGS.OPEN_AI.TITLE')"
+        icon="text-grammar-wand"
+        color-scheme="secondary"
+        variant="smooth"
+        size="small"
+        @click="toggleDropdown"
+      />
+      <div
+        v-if="showDropdown"
+        v-on-clickaway="closeDropdown"
+        class="dropdown-pane dropdown-pane--open ai-modal"
+      >
+        <h4 class="sub-block-title margin-top-1">
+          {{ $t('INTEGRATION_SETTINGS.OPEN_AI.TITLE') }}
+        </h4>
+        <p>
+          {{ $t('INTEGRATION_SETTINGS.OPEN_AI.SUBTITLE') }}
+        </p>
+        <label>
+          {{ $t('INTEGRATION_SETTINGS.OPEN_AI.TONE.TITLE') }}
+        </label>
+        <div class="tone__item">
+          <select v-model="activeTone" class="status--filter small">
+            <option v-for="tone in tones" :key="tone.key" :value="tone.key">
+              {{ tone.value }}
+            </option>
+          </select>
+        </div>
+        <div class="modal-footer flex-container align-right">
+          <woot-button variant="clear" size="small" @click="closeDropdown">
+            {{ $t('INTEGRATION_SETTINGS.OPEN_AI.BUTTONS.CANCEL') }}
+          </woot-button>
+          <woot-button
+            :is-loading="uiFlags.rephrase"
+            size="small"
+            @click="processEvent('rephrase')"
+          >
+            {{ buttonText }}
+          </woot-button>
+        </div>
       </div>
     </div>
   </div>
@@ -61,10 +86,18 @@ export default {
       type: String,
       default: '',
     },
+    isPrivateNote: {
+      type: Boolean,
+      default: false,
+    },
   },
   data() {
     return {
-      isGenerating: false,
+      uiFlags: {
+        rephrase: false,
+        reply_suggestion: false,
+        summarize: false,
+      },
       showDropdown: false,
       activeTone: 'professional',
       tones: [
@@ -94,7 +127,7 @@ export default {
       ).hooks[0].id;
     },
     buttonText() {
-      return this.isGenerating
+      return this.uiFlags.isRephrasing
         ? this.$t('INTEGRATION_SETTINGS.OPEN_AI.BUTTONS.GENERATING')
         : this.$t('INTEGRATION_SETTINGS.OPEN_AI.BUTTONS.GENERATE');
     },
@@ -111,14 +144,15 @@ export default {
     closeDropdown() {
       this.showDropdown = false;
     },
-    async processText() {
-      this.isGenerating = true;
+    async processEvent(type = 'rephrase') {
+      this.uiFlags[type] = true;
       try {
         const result = await OpenAPI.processEvent({
           hookId: this.hookId,
-          type: 'rephrase',
+          type,
           content: this.message,
           tone: this.activeTone,
+          conversationId: this.conversationId,
         });
         const {
           data: { message: generatedMessage },
@@ -128,7 +162,7 @@ export default {
       } catch (error) {
         this.showAlert(this.$t('INTEGRATION_SETTINGS.OPEN_AI.GENERATE_ERROR'));
       } finally {
-        this.isGenerating = false;
+        this.uiFlags[type] = false;
       }
     },
   },
diff --git a/app/javascript/dashboard/components/widgets/WootWriter/ReplyBottomPanel.vue b/app/javascript/dashboard/components/widgets/WootWriter/ReplyBottomPanel.vue
index 5f638d6dc..ccac0cd93 100644
--- a/app/javascript/dashboard/components/widgets/WootWriter/ReplyBottomPanel.vue
+++ b/app/javascript/dashboard/components/widgets/WootWriter/ReplyBottomPanel.vue
@@ -38,12 +38,12 @@
       </file-upload>
       <woot-button
         v-if="showAudioRecorderButton"
+        v-tooltip.top-end="$t('CONVERSATION.REPLYBOX.TIP_AUDIORECORDER_ICON')"
         :icon="!isRecordingAudio ? 'microphone' : 'microphone-off'"
         emoji="🎤"
         :color-scheme="!isRecordingAudio ? 'secondary' : 'alert'"
         variant="smooth"
         size="small"
-        :title="$t('CONVERSATION.REPLYBOX.TIP_AUDIORECORDER_ICON')"
         @click="toggleAudioRecorder"
       />
       <woot-button
@@ -92,8 +92,8 @@
         :conversation-id="conversationId"
       />
       <AIAssistanceButton
-        v-if="message"
         :conversation-id="conversationId"
+        :is-private-note="isOnPrivateNote"
         :message="message"
         @replace-text="replaceText"
       />
diff --git a/app/javascript/dashboard/i18n/locale/en/integrations.json b/app/javascript/dashboard/i18n/locale/en/integrations.json
index f37054878..3821fe6e8 100644
--- a/app/javascript/dashboard/i18n/locale/en/integrations.json
+++ b/app/javascript/dashboard/i18n/locale/en/integrations.json
@@ -84,6 +84,8 @@
     },
     "OPEN_AI": {
       "TITLE": "Improve With AI",
+      "SUMMARY_TITLE": "Summary with AI",
+      "REPLY_TITLE": "Reply suggestion with AI",
       "SUBTITLE": "An improved reply will be generated using AI, based on your current draft.",
       "TONE": {
         "TITLE": "Tone",
diff --git a/app/javascript/shared/components/FluentIcon/dashboard-icons.json b/app/javascript/shared/components/FluentIcon/dashboard-icons.json
index 42514a8fb..f19a9e57c 100644
--- a/app/javascript/shared/components/FluentIcon/dashboard-icons.json
+++ b/app/javascript/shared/components/FluentIcon/dashboard-icons.json
@@ -32,6 +32,10 @@
   "book-contacts-outline": "M15.5 12.25a.75.75 0 0 0-.75-.75h-5a.75.75 0 0 0-.75.75v.5c0 1 1.383 1.75 3.25 1.75s3.25-.75 3.25-1.75v-.5ZM14 8.745C14 7.78 13.217 7 12.25 7s-1.75.779-1.75 1.745a1.75 1.75 0 1 0 3.5 0ZM4 4.5A2.5 2.5 0 0 1 6.5 2H18a2.5 2.5 0 0 1 2.5 2.5v14.25a.75.75 0 0 1-.75.75H5.5a1 1 0 0 0 1 1h13.25a.75.75 0 0 1 0 1.5H6.5A2.5 2.5 0 0 1 4 19.5v-15Zm1.5 0V18H19V4.5a1 1 0 0 0-1-1H6.5a1 1 0 0 0-1 1Z",
   "book-open-globe-outline": "M3.5 5.75a.25.25 0 0 1 .25-.25H10c.69 0 1.25.56 1.25 1.25v8.959a6.49 6.49 0 0 1 1.5-2.646V6.75c0-.69.56-1.25 1.25-1.25h6.25a.25.25 0 0 1 .25.25v5.982A6.518 6.518 0 0 1 22 12.81V5.75A1.75 1.75 0 0 0 20.25 4H14c-.788 0-1.499.331-2 .863A2.742 2.742 0 0 0 10 4H3.75A1.75 1.75 0 0 0 2 5.75v12.5c0 .966.784 1.75 1.75 1.75H10c.495 0 .96-.13 1.36-.36a6.473 6.473 0 0 1-.343-1.663A1.248 1.248 0 0 1 10 18.5H3.75a.25.25 0 0 1-.25-.25V5.75ZM16.007 17c.04-1.415.248-2.669.553-3.585.171-.513.364-.893.554-1.134.195-.247.329-.281.386-.281.057 0 .192.034.386.281.19.241.383.62.554 1.134.305.916.513 2.17.553 3.585h-2.986Zm-.396-3.9c.108-.323.23-.622.368-.887A5.504 5.504 0 0 0 12.023 17h2.984c.04-1.5.26-2.866.604-3.9Zm3.778 0a6.133 6.133 0 0 0-.368-.887A5.504 5.504 0 0 1 22.978 17h-2.985c-.04-1.5-.26-2.866-.604-3.9Zm.604 4.9h2.985a5.504 5.504 0 0 1-3.957 4.787c.138-.265.26-.564.368-.886.345-1.035.564-2.4.604-3.901Zm-2.107 4.719c-.194.247-.329.281-.386.281-.057 0-.191-.034-.386-.281-.19-.241-.383-.62-.554-1.135-.305-.915-.513-2.17-.553-3.584h2.986c-.04 1.415-.248 2.669-.553 3.584-.171.514-.364.894-.554 1.135ZM12.023 18a5.504 5.504 0 0 0 3.956 4.787 6.133 6.133 0 0 1-.367-.886c-.346-1.035-.565-2.4-.605-3.901h-2.984Z",
   "book-outline": "M4 4.5A2.5 2.5 0 0 1 6.5 2H18a2.5 2.5 0 0 1 2.5 2.5v14.25a.75.75 0 0 1-.75.75H5.5a1 1 0 0 0 1 1h13.25a.75.75 0 0 1 0 1.5H6.5A2.5 2.5 0 0 1 4 19.5v-15ZM5.5 18H19V4.5a1 1 0 0 0-1-1H6.5a1 1 0 0 0-1 1V18Z",
+  "book-pulse-outline": [
+    "M11.69 7.458a.75.75 0 0 0-1.36-.043L8.785 10.5H7.75a.75.75 0 0 0 0 1.5h1.5a.75.75 0 0 0 .67-.415l1.023-2.044 2.116 5.001a.75.75 0 0 0 1.339.086L15.93 12h.819a.75.75 0 0 0 0-1.5H15.5a.75.75 0 0 0-.648.372l-.995 1.706-2.166-5.12Z",
+    "M6.5 2A2.5 2.5 0 0 0 4 4.5v15A2.5 2.5 0 0 0 6.5 22h13.25a.75.75 0 0 0 0-1.5H6.5a1 1 0 0 1-1-1h14.25a.75.75 0 0 0 .75-.75V4.5A2.5 2.5 0 0 0 18 2H6.5ZM19 18H5.5V4.5a1 1 0 0 1 1-1H18a1 1 0 0 1 1 1V18Z"
+  ],
   "bot-outline": "M17.753 14a2.25 2.25 0 0 1 2.25 2.25v.905a3.75 3.75 0 0 1-1.307 2.846C17.13 21.345 14.89 22 12 22c-2.89 0-5.128-.656-6.691-2a3.75 3.75 0 0 1-1.306-2.843v-.908A2.25 2.25 0 0 1 6.253 14h11.5Zm0 1.5h-11.5a.75.75 0 0 0-.75.75v.908c0 .655.286 1.278.784 1.706C7.545 19.945 9.44 20.502 12 20.502c2.56 0 4.458-.557 5.719-1.64a2.25 2.25 0 0 0 .784-1.706v-.906a.75.75 0 0 0-.75-.75ZM11.898 2.008 12 2a.75.75 0 0 1 .743.648l.007.102V3.5h3.5a2.25 2.25 0 0 1 2.25 2.25v4.505a2.25 2.25 0 0 1-2.25 2.25h-8.5a2.25 2.25 0 0 1-2.25-2.25V5.75A2.25 2.25 0 0 1 7.75 3.5h3.5v-.749a.75.75 0 0 1 .648-.743L12 2l-.102.007ZM16.25 5h-8.5a.75.75 0 0 0-.75.75v4.505c0 .414.336.75.75.75h8.5a.75.75 0 0 0 .75-.75V5.75a.75.75 0 0 0-.75-.75Zm-6.5 1.5a1.25 1.25 0 1 1 0 2.5 1.25 1.25 0 0 1 0-2.5Zm4.492 0a1.25 1.25 0 1 1 0 2.499 1.25 1.25 0 0 1 0-2.499Z",
   "brand-facebook-outline": "M24 12.073c0-6.627-5.373-12-12-12s-12 5.373-12 12c0 5.99 4.388 10.954 10.125 11.854v-8.385H7.078v-3.47h3.047V9.43c0-3.007 1.792-4.669 4.533-4.669 1.312 0 2.686.235 2.686.235v2.953H15.83c-1.491 0-1.956.925-1.956 1.874v2.25h3.328l-.532 3.47h-2.796v8.385C19.612 23.027 24 18.062 24 12.073z",
   "brand-instagram-outline": "M 8 3 C 5.243 3 3 5.243 3 8 L 3 16 C 3 18.757 5.243 21 8 21 L 16 21 C 18.757 21 21 18.757 21 16 L 21 8 C 21 5.243 18.757 3 16 3 L 8 3 z M 8 5 L 16 5 C 17.654 5 19 6.346 19 8 L 19 16 C 19 17.654 17.654 19 16 19 L 8 19 C 6.346 19 5 17.654 5 16 L 5 8 C 5 6.346 6.346 5 8 5 z M 17 6 A 1 1 0 0 0 16 7 A 1 1 0 0 0 17 8 A 1 1 0 0 0 18 7 A 1 1 0 0 0 17 6 z M 12 7 C 9.243 7 7 9.243 7 12 C 7 14.757 9.243 17 12 17 C 14.757 17 17 14.757 17 12 C 17 9.243 14.757 7 12 7 z M 12 9 C 13.654 9 15 10.346 15 12 C 15 13.654 13.654 15 12 15 C 10.346 15 9 13.654 9 12 C 9 10.346 10.346 9 12 9 z",
@@ -175,6 +179,10 @@
     "M8.78 1.22a.75.75 0 0 0-1.06 1.06l.72.72H6.25A3.25 3.25 0 0 0 3 6.25v2.19l-.72-.72a.75.75 0 0 0-1.06 1.06l2 2a.748.748 0 0 0 1.06 0l2-2a.747.747 0 0 0 0-1.06.75.75 0 0 0-1.06 0l-.72.72V6.25c0-.966.784-1.75 1.75-1.75h2.19l-.72.72a.75.75 0 0 0 .78 1.237.75.75 0 0 0 .28-.177l2-2a.75.75 0 0 0 0-1.06l-2-2Z",
     "M11.832 3a1.755 1.755 0 0 1 0 1.5H14v4h-4V6.475l-.513.512a1.742 1.742 0 0 1-.987.495V8.5H7.482c-.052.361-.217.71-.495.987L6.475 10H8.5v4h-4v-2.168a1.755 1.755 0 0 1-1.5 0v5.918A3.25 3.25 0 0 0 6.25 21h11.5A3.25 3.25 0 0 0 21 17.75V6.25A3.25 3.25 0 0 0 17.75 3h-5.918ZM10 14v-4h4v4h-4Zm5.5 0v-4h4v4h-4ZM14 15.5v4h-4v-4h4Zm1.5 4v-4h4v2.25a1.75 1.75 0 0 1-1.75 1.75H15.5Zm0-11v-4h2.25c.966 0 1.75.784 1.75 1.75V8.5h-4Zm-11 7h4v4H6.25a1.75 1.75 0 0 1-1.75-1.75V15.5Z"
   ],
+  "text-grammar-wand-outline": [
+    "M2.75 17h7.775l-1.5 1.5H2.75a.75.75 0 0 1-.102-1.493L2.75 17ZM2.75 14.5h7.564a1.745 1.745 0 0 1-.241-1.5H2.75l-.102.007A.75.75 0 0 0 2.75 14.5ZM12.72 16.22a.75.75 0 1 1 1.06 1.06l-4.5 4.5a.75.75 0 0 1-1.06-1.06l4.5-4.5ZM2.75 9h10.5a.75.75 0 0 1 .102 1.493l-.102.007H2.75a.75.75 0 0 1-.102-1.493L2.75 9ZM2.75 5h18.5a.75.75 0 0 1 .102 1.493l-.102.007H2.75a.75.75 0 0 1-.102-1.493L2.75 5Z",
+    "M16.5 8a.75.75 0 0 1 .744.658l.14 1.13a3.25 3.25 0 0 0 2.828 2.829l1.13.139a.75.75 0 0 1 0 1.488l-1.13.14a3.25 3.25 0 0 0-2.829 2.828l-.139 1.13a.75.75 0 0 1-1.488 0l-.14-1.13a3.25 3.25 0 0 0-2.828-2.829l-1.13-.139a.75.75 0 0 1 0-1.488l1.13-.14a3.25 3.25 0 0 0 2.829-2.828l.139-1.13A.75.75 0 0 1 16.5 8Zm0 3.774a4.761 4.761 0 0 1-1.726 1.726 4.761 4.761 0 0 1 1.726 1.726 4.761 4.761 0 0 1 1.726-1.726 4.761 4.761 0 0 1-1.726-1.726Z"
+  ],
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diff --git a/app/javascript/shared/components/Spinner.vue b/app/javascript/shared/components/Spinner.vue
index de60b680b..ec02b05cb 100644
--- a/app/javascript/shared/components/Spinner.vue
+++ b/app/javascript/shared/components/Spinner.vue
@@ -1,5 +1,5 @@
 <template>
-  <span class="spinner" :class="size" />
+  <span class="spinner" :class="`${size} ${colorScheme}`" />
 </template>
 <script>
 export default {
@@ -8,6 +8,10 @@ export default {
       type: String,
       default: 'small',
     },
+    colorScheme: {
+      type: String,
+      default: '',
+    },
   },
 };
 </script>
@@ -32,8 +36,8 @@ export default {
     margin-top: -$space-one;
     margin-left: -$space-one;
     border-radius: 50%;
-    border: 2px solid rgba(255, 255, 255, 0.7);
-    border-top-color: rgba(255, 255, 255, 0.2);
+    border: 2px solid rgba(255, 255, 255, 0.8);
+    border-top-color: rgba(255, 255, 255, 0.3);
     animation: spinner 0.9s linear infinite;
   }
 }
@@ -84,5 +88,10 @@ export default {
       margin-top: -$space-small + $space-micro;
     }
   }
+
+  &.dark::before {
+    border-color: rgba(0, 0, 0, 0.7);
+    border-top-color: rgba(0, 0, 0, 0.2);
+  }
 }
 </style>
diff --git a/app/javascript/shared/components/specs/__snapshots__/Spinner.spec.js.snap b/app/javascript/shared/components/specs/__snapshots__/Spinner.spec.js.snap
index 4c2f77a5d..9eccfc523 100644
--- a/app/javascript/shared/components/specs/__snapshots__/Spinner.spec.js.snap
+++ b/app/javascript/shared/components/specs/__snapshots__/Spinner.spec.js.snap
@@ -2,6 +2,6 @@
 
 exports[`Spinner matches snapshot 1`] = `
 <span
-  class="spinner small"
+  class="spinner small "
 />
 `;
diff --git a/lib/integrations/openai/processor_service.rb b/lib/integrations/openai/processor_service.rb
index 54d2e5ac5..84afad27a 100644
--- a/lib/integrations/openai/processor_service.rb
+++ b/lib/integrations/openai/processor_service.rb
@@ -35,20 +35,48 @@ class Integrations::Openai::ProcessorService
   end
 
   def conversation_messages(in_array_format: false)
-    conversation = hook.account.conversations.find_by(display_id: event['data']['conversation_display_id'])
-    messages = in_array_format ? [] : ''
+    conversation = find_conversation
+    messages = init_messages_body(in_array_format)
+
+    add_messages_until_token_limit(conversation, messages, in_array_format)
+  end
+
+  def find_conversation
+    hook.account.conversations.find_by(display_id: event['data']['conversation_display_id'])
+  end
+
+  def add_messages_until_token_limit(conversation, messages, in_array_format)
     character_count = 0
-
     conversation.messages.chat.reorder('id desc').each do |message|
-      character_count += message.content.length
-      break if character_count > TOKEN_LIMIT
-
-      formatted_message = format_message(message, in_array_format)
-      messages.prepend(formatted_message)
+      character_count, message_added = add_message_if_within_limit(character_count, message, messages, in_array_format)
+      break unless message_added
     end
     messages
   end
 
+  def add_message_if_within_limit(character_count, message, messages, in_array_format)
+    if valid_message?(message, character_count)
+      add_message_to_list(message, messages, in_array_format)
+      character_count += message.content.length
+      [character_count, true]
+    else
+      [character_count, false]
+    end
+  end
+
+  def valid_message?(message, character_count)
+    message.content.present? && character_count + message.content.length <= TOKEN_LIMIT
+  end
+
+  def add_message_to_list(message, messages, in_array_format)
+    formatted_message = format_message(message, in_array_format)
+    messages.prepend(formatted_message)
+  end
+
+  def init_messages_body(in_array_format)
+    in_array_format ? [] : ''
+  end
+
   def format_message(message, in_array_format)
     in_array_format ? format_message_in_array(message) : format_message_in_string(message)
   end