diff --git a/modules/ROOT/pages/dialog-footer-buttons.adoc b/modules/ROOT/pages/dialog-footer-buttons.adoc
index 4cd569b796..a26fcd6c56 100644
--- a/modules/ROOT/pages/dialog-footer-buttons.adoc
+++ b/modules/ROOT/pages/dialog-footer-buttons.adoc
@@ -16,7 +16,8 @@ NOTE: Dialog footer buttons are different to xref:dialog-components.adoc#button[
 |text |string |required |Text to display in the button if `+icon+` is not specified. Also used for the button's `+title+` attribute.
 |name |string |optional |An identifier for the button. If not specified, the button will be assigned a randomly generated `+name+`.
 |icon |string |optional |
-include::partial$misc/admon-predefined-icons-only.adoc[] *When configured, the button will display the icon instead of text.*
+include::partial$misc/admon-predefined-icons-only.adoc[]
+*When configured, the button will display the icon instead of text.*
 |buttonType |`+'primary'+`, or `+'secondary'+` |optional |default: `+'secondary'+` - Whether to style the button as a primary, or secondary button.
 |enabled |boolean |optional |default: `+true+` - When `+false+`, the button will be disabled when the dialog loads.
 |align |`+'end'+` or `+'start'+` |optional |default: `+'end'+` - When set to `+'end'+` the button will display on the right-hand side of the dialog. When set to `+'start'+` the button will display on the left-hand side.
diff --git a/modules/ROOT/partials/configuration/ai_request.adoc b/modules/ROOT/partials/configuration/ai_request.adoc
index fce72c8f28..4343cfd330 100644
--- a/modules/ROOT/partials/configuration/ai_request.adoc
+++ b/modules/ROOT/partials/configuration/ai_request.adoc
@@ -40,6 +40,18 @@ tinymce.init({
           return [];
         }
       });
+	  
+      // System messages provided by the plugin to format the output as HTML content.
+      const pluginSystemMessages = request.system.map((content) => ({
+        role: 'system',
+        content
+      }));
+      
+      const systemMessages = [
+        ...pluginSystemMessages,
+        // Additional system messages to control the output of the AI
+        { role: 'system', content: 'Remove lines with ``` from the response start and response end.' }
+      ]
 
       // Forms the new query sent to the API
       const content = request.context.length === 0 || conversation.length > 0
@@ -48,7 +60,7 @@ tinymce.init({
 
       const messages = [
         ...conversation,
-        { role: 'system', content: request.system.join('\n') },
+        ...systemMessages,
         { role: 'user', content }
       ];
 
@@ -116,7 +128,7 @@ tinymce.init({
           onerror
         })
       )
-      .then((response) => {
+      .then(async (response) => {
         if (response && !response.ok) {
           const data = await response.json();
           if (data.error) {
diff --git a/modules/ROOT/partials/configuration/ai_shortcuts.adoc b/modules/ROOT/partials/configuration/ai_shortcuts.adoc
index 7e042f2331..44a48cd4ae 100644
--- a/modules/ROOT/partials/configuration/ai_shortcuts.adoc
+++ b/modules/ROOT/partials/configuration/ai_shortcuts.adoc
@@ -19,25 +19,25 @@ When configured with an instance-specific object array, the {pluginname} shortcu
 [source, js]
 ----
 [
-  { title: 'Summarize content', prompt: 'Provide the key points and concepts in this content in a succinct summary.' },
-  { title: 'Improve writing', prompt: 'Rewrite this content with no spelling mistakes, proper grammar, and with more descriptive language, using best writing practices without losing the original meaning.' },
-  { title: 'Simplify language', prompt: 'Rewrite this content with simplified language and reduce the complexity of the writing, so that the content is easier to understand.' },
-  { title: 'Expand upon', prompt: 'Expand upon this content with descriptive language and more detailed explanations, to make the writing easier to understand and increase the length of the content.' },
-  { title: 'Trim content', prompt: 'Remove any repetitive, redundant, or non-essential writing in this content without changing the meaning or losing any key information.' },
+  { title: 'Summarize content', prompt: 'Provide the key points and concepts in this content in a succinct summary.', selection: true },
+  { title: 'Improve writing', prompt: 'Rewrite this content with no spelling mistakes, proper grammar, and with more descriptive language, using best writing practices without losing the original meaning.', selection: true },
+  { title: 'Simplify language', prompt: 'Rewrite this content with simplified language and reduce the complexity of the writing, so that the content is easier to understand.', selection: true },
+  { title: 'Expand upon', prompt: 'Expand upon this content with descriptive language and more detailed explanations, to make the writing easier to understand and increase the length of the content.', selection: true },
+  { title: 'Trim content', prompt: 'Remove any repetitive, redundant, or non-essential writing in this content without changing the meaning or losing any key information.', selection: true },
   { title: 'Change tone', subprompts: [
-    { title: 'Professional', prompt: 'Rewrite this content using polished, formal, and respectful language to convey professional expertise and competence.' },
-    { title: 'Casual', prompt: 'Rewrite this content with casual, informal language to convey a casual conversation with a real person.' },
-    { title: 'Direct', prompt: 'Rewrite this content with direct language using only the essential information.' },
-    { title: 'Confident', prompt: 'Rewrite this content using compelling, optimistic language to convey confidence in the writing.' },
-    { title: 'Friendly', prompt: 'Rewrite this content using friendly, comforting language, to convey understanding and empathy.' },
+    { title: 'Professional', prompt: 'Rewrite this content using polished, formal, and respectful language to convey professional expertise and competence.', selection: true },
+    { title: 'Casual', prompt: 'Rewrite this content with casual, informal language to convey a casual conversation with a real person.', selection: true },
+    { title: 'Direct', prompt: 'Rewrite this content with direct language using only the essential information.', selection: true },
+    { title: 'Confident', prompt: 'Rewrite this content using compelling, optimistic language to convey confidence in the writing.', selection: true },
+    { title: 'Friendly', prompt: 'Rewrite this content using friendly, comforting language, to convey understanding and empathy.', selection: true },
   ] },
   { title: 'Change style', subprompts: [
-    { title: 'Business', prompt: 'Rewrite this content as a business professional with formal language.' },
-    { title: 'Legal', prompt: 'Rewrite this content as a legal professional using valid legal terminology.' },
-    { title: 'Journalism', prompt: 'Rewrite this content as a journalist using engaging language to convey the importance of the information.' },
-    { title: 'Medical', prompt: 'Rewrite this content as a medical professional using valid medical terminology.' },
-    { title: 'Poetic', prompt: 'Rewrite this content as a poem using poetic techniques without losing the original meaning.' },
-  ] },
+    { title: 'Business', prompt: 'Rewrite this content as a business professional with formal language.', selection: true },
+    { title: 'Legal', prompt: 'Rewrite this content as a legal professional using valid legal terminology.', selection: true },
+    { title: 'Journalism', prompt: 'Rewrite this content as a journalist using engaging language to convey the importance of the information.', selection: true },
+    { title: 'Medical', prompt: 'Rewrite this content as a medical professional using valid medical terminology.', selection: true },
+    { title: 'Poetic', prompt: 'Rewrite this content as a poem using poetic techniques without losing the original meaning.', selection: true },
+  ] }
 ]
 ----
 
@@ -59,18 +59,18 @@ tinymce.init({
   toolbar: 'aidialog aishortcuts',
   ai_request: (request, respondWith) => respondWith.string(() => Promise.reject("See docs to implement AI Assistant")),
   ai_shortcuts: [
-    { title: 'Screenplay', prompt: 'Convert this to screenplay format.' },
-    { title: 'Stage play', prompt: 'Convert this to stage play format.' },
+    { title: 'Screenplay', prompt: 'Convert this to screenplay format.', selection: true },
+    { title: 'Stage play', prompt: 'Convert this to stage play format.', selection: true },
     { title: 'Classical', subprompts: 
       [
-        { title: 'Dialogue', prompt: 'Convert this to a Socratic dialogue.' },
-        { title: 'Homeric', prompt: 'Convert this to a Classical Epic.' }
+        { title: 'Dialogue', prompt: 'Convert this to a Socratic dialogue.', selection: true },
+        { title: 'Homeric', prompt: 'Convert this to a Classical Epic.', selection: true }
       ]
     },
     { title: 'Celtic', subprompts:
       [
-        { title: 'Bardic', prompt: 'Convert this to Bardic verse.' },
-        { title: 'Filí', prompt: 'Convert this to Filí-an verse.' }
+        { title: 'Bardic', prompt: 'Convert this to Bardic verse.', selection: true },
+        { title: 'Filí', prompt: 'Convert this to Filí-an verse.', selection: true }
       ]
     },
   ]
@@ -99,14 +99,31 @@ tinymce.init({
 
 === Valid Shortcuts
 
-Valid shortcut objects contain the following fields.
+Valid shortcut objects contain the following properties.
 
 `+title+`:: A string which is displayed in the `+aishortcuts+` toolbar button and menu item. This will indicate which shortcut is used, or which category of shortcuts are in this menu.
 
 And either
 
-`+prompt+`:: A string containing the query which is given to the `+ai_request+` function when the shortcut is used.
+`+subprompts+`:: An array containing more valid shortcut objects. This allows shortcuts to be grouped into categories within the {pluginname} shortcuts toolbar button and menu item.
 
 or
 
-`+subprompts+`:: An array containing more valid shortcut objects. This allows shortcuts to be grouped into categories within the {pluginname} shortcuts toolbar button and menu item.
\ No newline at end of file
+`+prompt+`:: A string containing the query which is given to the `+ai_request+` function when the shortcut is used.
+
+
+==== The `+selection+` property
+
+include::partial$misc/admon-requires-6.8v.adoc[]
+
+Shortcut objects with the `+prompt+` property may also contain the following optional property.
+
+`+selection+`:: A boolean value which will match to the current selection and set the enabled state of the shortcut. When `+selection+` is:
+
+* `+true+`: The shortcut will _only_ be enabled when the user _has_ made a selection in the editor.
+
+* `+false+`: The shortcut will _only_ be enabled when the user _has not_ made a selection in the editor.
+
+* `+undefined+`, or _not set_: The shortcut will always be enabled.
+
+This property allows the definition of shortcuts which should only operate when the user has selected content, requiring the selection as context to the AI when the property is `+true+`. Additionally, shortcuts which are intended to generate specific content will not be enabled with any selection when the property if `+false+`.