diff --git a/lib/account.js b/lib/account.js
index c0e0fae7..7fcc4f9d 100644
--- a/lib/account.js
+++ b/lib/account.js
@@ -1741,7 +1741,7 @@ class Account {
                         }
                     };
 
-                    for (let indexName of [index, `${index}.threads`]) {
+                    for (let indexName of [index, `${index}.threads`, `${index}.embeddings`]) {
                         try {
                             deleteResult[indexName] = await client.deleteByQuery({
                                 index: indexName,
diff --git a/views/config/ai.hbs b/views/config/ai.hbs
index c2f741a6..01e8c099 100644
--- a/views/config/ai.hbs
+++ b/views/config/ai.hbs
@@ -78,15 +78,15 @@
                         id="openAiGenerateEmbeddings" name="openAiGenerateEmbeddings" {{#if
                         values.openAiGenerateEmbeddings}}checked{{/if}} />
                     <label class="form-check-label" for="openAiGenerateEmbeddings">Generate vector embeddings for
-                        the
-                        email using OpenAI API.</label>
+                        the email using OpenAI API.</label>
                     {{#if errors.openAiGenerateEmbeddings}}
                     <span class="invalid-feedback">{{errors.openAiGenerateEmbeddings}}</span>
                     {{/if}}
                     <small class="form-text text-muted">EmailEngine uses OpenAI API to generate text embeddings for
                         new emails. To decrease vector size, EmailEngine splits email text into chunks of up to 600
                         tokens and generates embeddings for each chunk separately. Embeddings are only available in
-                        <code>messageNew</code> webhooks, and these are not stored in the Document Store.</small>
+                        <code>messageNew</code> webhooks, and these are not stored in the Document Store by
+                        default.</small>
                 </div>
 
                 <div class="text-right">
diff --git a/views/config/document-store/index.hbs b/views/config/document-store/index.hbs
index 37b46e3e..28d46d26 100644
--- a/views/config/document-store/index.hbs
+++ b/views/config/document-store/index.hbs
@@ -49,21 +49,70 @@
                 </div>
             </div>
         </div>
-        <div class="card-body">
 
-            <div class="form-group form-check">
-                <div class="text-muted float-right code-link">[<a href="/admin/iframe/docs#/settings/postV1Settings"
-                        target="_blank">documentStoreEnabled</a>]
+        <ul class="list-group list-group-flush mb-3">
+            <li class="list-group-item d-flex justify-content-between align-items-top">
+
+                <div class="form-group form-check mb-0">
+                    <input type="checkbox" class="form-check-input {{#if errors.documentStoreEnabled}}is-invalid{{/if}}"
+                        id="documentStoreEnabled" name="documentStoreEnabled" {{#if
+                        values.documentStoreEnabled}}checked{{/if}} />
+                    <label class="form-check-label" for="documentStoreEnabled">Enable syncing to the Document
+                        Store.</label>
+                    {{#if errors.documentStoreEnabled}}
+                    <span class="invalid-feedback">{{errors.documentStoreEnabled}}</span>
+                    {{/if}}
+                    <small class="form-text text-muted">If enabled, then EmailEngine stores structured email content to
+                        ElasticSearch. Stored data does include attachment metadata but not attachment contents.
+                        <i>Enabling this option does not apply to already processed emails.</i></small>
                 </div>
 
-                <input type="checkbox" class="form-check-input {{#if errors.documentStoreEnabled}}is-invalid{{/if}}"
-                    id="documentStoreEnabled" name="documentStoreEnabled" {{#if
-                    values.documentStoreEnabled}}checked{{/if}} />
-                <label class="form-check-label" for="documentStoreEnabled">Enable syncing to the Document Store</label>
-                {{#if errors.documentStoreEnabled}}
-                <span class="invalid-feedback">{{errors.documentStoreEnabled}}</span>
-                {{/if}}
-            </div>
+                <div class="text-right">
+                    <div class="text-muted code-link">[<a href="/admin/iframe/docs#/settings/postV1Settings"
+                            target="_blank">documentStoreEnabled</a>]</div>
+
+                    {{#if
+                    values.documentStoreEnabled}}
+                    <span class="badge badge-success badge-pill">enabled</span>
+                    {{else}}
+                    <span class="badge badge-warning badge-pill">disabled</span>
+                    {{/if}}
+                </div>
+            </li>
+
+            <li class="list-group-item d-flex justify-content-between align-items-top">
+
+                <div class="form-group form-check mb-0">
+                    <input type="checkbox"
+                        class="form-check-input {{#if errors.documentStoreGenerateEmbeddings}}is-invalid{{/if}}"
+                        id="documentStoreGenerateEmbeddings" name="documentStoreGenerateEmbeddings" {{#if
+                        values.documentStoreGenerateEmbeddings}}checked{{/if}} />
+                    <label class="form-check-label" for="documentStoreGenerateEmbeddings">Enable the "Chat with email"
+                        feature.</label>
+                    {{#if errors.documentStoreGenerateEmbeddings}}
+                    <span class="invalid-feedback">{{errors.documentStoreGenerateEmbeddings}}</span>
+                    {{/if}}
+                    <small class="form-text text-muted">If enabled, then EmailEngine uses OpenAI API to generate text
+                        embeddings for emails stored in the document store. This option requires document store syncing
+                        to be enabled and the OpenAI API key to be set <a href="/admin/config/ai">here</a>. <i>Enabling
+                            this option does not apply to already processed emails.</i></small>
+                </div>
+
+                <div class="text-right">
+                    <div class="text-muted code-link">[<a href="/admin/iframe/docs#/settings/postV1Settings"
+                            target="_blank">documentStoreGenerateEmbeddings</a>]</div>
+
+                    {{#if
+                    values.documentStoreGenerateEmbeddings}}
+                    <span class="badge badge-success badge-pill">enabled</span>
+                    {{else}}
+                    <span class="badge badge-warning badge-pill">disabled</span>
+                    {{/if}}
+                </div>
+            </li>
+        </ul>
+
+        <div class="card-body">
 
             <div class="form-group">
                 <div class="text-muted float-right code-link">[<a href="/admin/iframe/docs#/settings/postV1Settings"
diff --git a/workers/documents.js b/workers/documents.js
index 43005742..103ea0a7 100644
--- a/workers/documents.js
+++ b/workers/documents.js
@@ -160,7 +160,7 @@ const documentsWorker = new Worker(
                         }
                     };
 
-                    for (let indexName of [index, `${index}.threads`]) {
+                    for (let indexName of [index, `${index}.threads`, `${index}.embeddings`]) {
                         try {
                             deleteResult[indexName] = await client.deleteByQuery({
                                 index: indexName,
@@ -552,6 +552,9 @@ const documentsWorker = new Worker(
                     }
                 }
 
+                // remove from embeddings delete queue
+                await redis.zrem(`${REDIS_PREFIX}expungequeue`, `${job.data.account}:${messageId}`);
+
                 return {
                     index: indexResult._index,
                     id: indexResult._id,
@@ -582,6 +585,9 @@ const documentsWorker = new Worker(
                             index,
                             id: `${job.data.account}:${messageId}`
                         });
+
+                        // add to embeddings delete queue
+                        await redis.zadd(`${REDIS_PREFIX}expungequeue`, Date.now(), `${job.data.account}:${messageId}`);
                     } catch (err) {
                         switch (err.meta && err.meta.body && err.meta.body.result) {
                             case 'not_found':