diff --git a/packages/super-editor/src/core/super-converter/exporter.js b/packages/super-editor/src/core/super-converter/exporter.js
index 20ceb55559..9c8468c329 100644
--- a/packages/super-editor/src/core/super-converter/exporter.js
+++ b/packages/super-editor/src/core/super-converter/exporter.js
@@ -1731,17 +1731,25 @@ function prepareCheckboxAnnotation(params) {
  */
 function prepareHtmlAnnotation(params) {
   const {
-    node: { attrs = {} },
+    node: { attrs = {}, marks = [] },
+    editorSchema,
   } = params;
 
   const parser = new window.DOMParser();
   const paragraphHtml = parser.parseFromString(attrs.rawHtml || attrs.displayLabel, 'text/html');
+  const marksFromAttrs = translateFieldAttrsToMarks(attrs);
+  const allMarks = [...marks, ...marksFromAttrs]
 
-  const state = EditorState.create({
-    doc: PMDOMParser.fromSchema(params.editorSchema).parse(paragraphHtml),
+  let state = EditorState.create({
+    doc: PMDOMParser.fromSchema(editorSchema).parse(paragraphHtml),
   });
 
+  if (allMarks.length) {
+    state = applyMarksToHtmlAnnotation(state, allMarks);
+  }
+
   const htmlAnnotationNode = state.doc.toJSON();
+  
   return {
     name: 'htmlAnnotation',
     elements: translateChildNodes({
@@ -1896,6 +1904,20 @@ function translateFieldAnnotation(params) {
               'w:val': attrs.multipleImage,
             },
           },
+          {
+            name: 'w:fieldFontFamily',
+            attributes: {
+              'xmlns:w': customXmlns,
+              'w:val': attrs.fontFamily,
+            },
+          },
+          {
+            name: 'w:fieldFontSize',
+            attributes: {
+              'xmlns:w': customXmlns,
+              'w:val': attrs.fontSize,
+            },
+          },
         ],
       },
       {
@@ -2103,3 +2125,46 @@ function resizeKeepAspectRatio(width, height, maxWidth) {
   }
   return { width, height };
 }
+
+function applyMarksToHtmlAnnotation(state, marks) {
+  const { tr, doc, schema } = state;
+  const allowedMarks = ['fontFamily', 'fontSize'];
+
+  if (
+    !marks.some((m) => allowedMarks.includes(m.type))
+  ) {
+    return state;
+  }
+
+  const fontFamily = marks.find((m) => m.type === 'fontFamily');
+  const fontSize = marks.find((m) => m.type === 'fontSize');
+
+  doc.descendants((node, pos) => {
+    if (!node.isText) return;
+
+    const found = node.marks.find((m) => m.type.name === 'textStyle');
+    const textStyleType = schema.marks.textStyle;
+
+    if (!found) {
+      tr.addMark(pos, pos + node.nodeSize, textStyleType.create({
+        ...fontFamily?.attrs,
+        ...fontSize?.attrs,
+      }));
+      return;
+    }
+
+    if (!found?.attrs.fontFamily && fontFamily) {
+      tr.addMark(pos, pos + node.nodeSize, textStyleType.create({
+        ...found?.attrs,
+        ...fontFamily.attrs,
+      }));
+    } else if (!found?.attrs.fontSize && fontSize) {
+      tr.addMark(pos, pos + node.nodeSize, textStyleType.create({
+        ...found?.attrs,
+        ...fontSize.attrs,
+      }));
+    }
+  });
+
+  return state.apply(tr);
+};
diff --git a/packages/super-editor/src/core/super-converter/v2/importer/annotationImporter.js b/packages/super-editor/src/core/super-converter/v2/importer/annotationImporter.js
index d097292057..1c88fdee2b 100644
--- a/packages/super-editor/src/core/super-converter/v2/importer/annotationImporter.js
+++ b/packages/super-editor/src/core/super-converter/v2/importer/annotationImporter.js
@@ -13,7 +13,8 @@ export const handleAnnotationNode = (params) => {
   const node = nodes[0];
   const sdtPr = node.elements.find((el) => el.name === 'w:sdtPr');
   const sdtContent = node.elements.find((el) => el.name === 'w:sdtContent');
-  const { attrs: marksAsAttrs, marks } = parseAnnotationMarks(sdtContent);
+  const type = sdtPr?.elements.find((el) => el.name === 'w:fieldTypeShort')?.attributes['w:val'];
+  const { attrs: marksAsAttrs, marks } = parseAnnotationMarks(sdtContent, type);
 
   const docPartObj = sdtPr?.elements.find((el) => el.name === 'w:docPartObj');
   if (docPartObj) {
@@ -23,9 +24,10 @@ export const handleAnnotationNode = (params) => {
   const alias = sdtPr?.elements.find((el) => el.name === 'w:alias');
   const tag = sdtPr?.elements.find((el) => el.name === 'w:tag');
   const fieldType = sdtPr?.elements.find((el) => el.name === 'w:fieldType')?.attributes['w:val'];
-  const type = sdtPr?.elements.find((el) => el.name === 'w:fieldTypeShort')?.attributes['w:val'];
   const fieldColor = sdtPr?.elements.find((el) => el.name === 'w:fieldColor')?.attributes['w:val'];
   const isMultipleImage = sdtPr?.elements.find((el) => el.name === 'w:fieldMultipleImage')?.attributes['w:val'];
+  const fontFamily = sdtPr?.elements.find((el) => el.name === 'w:fieldFontFamily')?.attributes['w:val'];
+  const fontSize = sdtPr?.elements.find((el) => el.name === 'w:fieldFontSize')?.attributes['w:val'];
 
   const attrs = {
     type,
@@ -34,8 +36,12 @@ export const handleAnnotationNode = (params) => {
     fieldType,
     fieldColor,
     multipleImage: isMultipleImage === 'true',
+    fontFamily: fontFamily !== 'null' ? fontFamily : null,
+    fontSize: fontSize !== 'null' ? fontSize : null,
   };
 
+  const allAttrs = { ...attrs, ...marksAsAttrs };
+
   if (!attrs.fieldId || !attrs.displayLabel) {
     return { nodes: [], consumed: 0 };
   }
@@ -43,14 +49,14 @@ export const handleAnnotationNode = (params) => {
   let result = {
     type: 'text',
     text: `{{${attrs.displayLabel}}}`,
-    attrs: { ...attrs, ...marksAsAttrs },
+    attrs: allAttrs,
     marks,
   };
   
   if (params.editor.options.annotations) {
     result = {
       type: 'fieldAnnotation',
-      attrs: { ...attrs, ...marksAsAttrs }
+      attrs: allAttrs,
     };
   };
   
@@ -65,8 +71,20 @@ export const handleAnnotationNode = (params) => {
  * @param {Object} content The sdtContent node
  * @returns {Object} The attributes object
  */
-export const parseAnnotationMarks = (content = {}) => {
-  const run = content.elements?.find((el) => el.name === 'w:r');
+export const parseAnnotationMarks = (content = {}, type) => {
+  let mainContent = content;
+
+  if (type === 'html') {
+    /// Note: html annotation has a different structure and can include 
+    /// several paragraphs with different styles. We could find the first paragraph 
+    /// and take the marks from there, but we take fontFamily and fontSize from the annotation attributes.
+
+    /// Example: 
+    /// const firstPar = content.elements?.find((el) => el.name === 'w:p');
+    /// if (firstPar) mainContent = firstPar;
+  }
+
+  const run = mainContent.elements?.find((el) => el.name === 'w:r');
   const rPr = run?.elements?.find((el) => el.name === 'w:rPr');
   if (!rPr) return {};
 
diff --git a/packages/super-editor/src/dev/components/DeveloperPlayground.vue b/packages/super-editor/src/dev/components/DeveloperPlayground.vue
index dddd72a6dc..c04057ffc1 100644
--- a/packages/super-editor/src/dev/components/DeveloperPlayground.vue
+++ b/packages/super-editor/src/dev/components/DeveloperPlayground.vue
@@ -45,6 +45,15 @@ const onCreate = ({ editor }) => {
 
   // Set debugging pagination value from editor plugin state
   isDebuggingPagination.value = PaginationPluginKey.getState(editor.state)?.isDebugging;
+
+  // editor.commands.addFieldAnnotation(0, {
+  //   type: 'html',
+  //   displayLabel: 'Paragraph',
+  //   fieldId: `123`,
+  //   fieldType: 'TEXTINPUT',
+  //   fieldColor: '#980043',
+  //   rawHtml: '<p><span style="font-family: Courier New; font-size: 8pt;">Par 1</span></p><p>Par 2</p>',
+  // });
 };
 
 const onCommentClicked = ({ conversation }) => {
@@ -68,6 +77,7 @@ const editorOptions = computed(() => {
     users: [], // For comment @-mentions, only users that have access to the document
     pagination: true,
     telemetry: telemetry.value,
+    annotations: true,
   }
 });