diff --git a/packages/super-editor/src/components/toolbar/super-toolbar.js b/packages/super-editor/src/components/toolbar/super-toolbar.js
index 6d58932723..3b2d455bb8 100644
--- a/packages/super-editor/src/components/toolbar/super-toolbar.js
+++ b/packages/super-editor/src/components/toolbar/super-toolbar.js
@@ -20,6 +20,7 @@ import { isList } from '@core/commands/list-helpers';
 import { calculateResolvedParagraphProperties } from '@extensions/paragraph/resolvedPropertiesCache.js';
 import { twipsToLines } from '@converter/helpers';
 import { parseSizeUnit } from '@core/utilities';
+import { encodeMarksFromRPr } from '@core/super-converter/styles.js';
 import { NodeSelection } from 'prosemirror-state';
 
 /**
@@ -899,9 +900,16 @@ export class SuperToolbar extends EventEmitter {
           state.doc.resolve(paragraphParent.pos),
         )
       : null;
+    const selectionIsCollapsed = selection.empty;
+    const paragraphIsEmpty = paragraphParent?.node?.content?.size === 0;
+    const paragraphFontFamily = getParagraphFontFamilyFromProperties(
+      paragraphProps,
+      this.activeEditor?.converter?.convertedXml ?? {},
+    );
 
     this.toolbarItems.forEach((item) => {
       item.resetDisabled();
+      let activatedFromLinkedStyle = false;
 
       if (item.name.value === 'undo') {
         item.setDisabled(this.undoDepth === 0);
@@ -966,12 +974,25 @@ export class SuperToolbar extends EventEmitter {
             [item.name.value]: linkedStylesItem,
           };
           item.activate(value);
+          activatedFromLinkedStyle = true;
         }
       }
       if (item.name.value === 'textAlign' && paragraphProps?.justification) {
         item.activate({ textAlign: paragraphProps.justification });
       }
 
+      if (
+        item.name.value === 'fontFamily' &&
+        selectionIsCollapsed &&
+        paragraphIsEmpty &&
+        !activeMark &&
+        !markNegated &&
+        !activatedFromLinkedStyle &&
+        paragraphFontFamily
+      ) {
+        item.activate({ fontFamily: paragraphFontFamily });
+      }
+
       if (item.name.value === 'lineHeight') {
         if (paragraphProps?.spacing) {
           item.selectedValue.value = twipsToLines(paragraphProps.spacing.line);
@@ -1358,3 +1379,10 @@ export class SuperToolbar extends EventEmitter {
     }
   }
 }
+
+function getParagraphFontFamilyFromProperties(paragraphProps, convertedXml = {}) {
+  const fontFamilyProps = paragraphProps?.runProperties?.fontFamily;
+  if (!fontFamilyProps) return null;
+  const [markDef] = encodeMarksFromRPr({ fontFamily: fontFamilyProps }, convertedXml);
+  return markDef?.attrs?.fontFamily ?? null;
+}
diff --git a/packages/super-editor/src/tests/toolbar/updateToolbarState.test.js b/packages/super-editor/src/tests/toolbar/updateToolbarState.test.js
index 3735abe2e0..934f00dcee 100644
--- a/packages/super-editor/src/tests/toolbar/updateToolbarState.test.js
+++ b/packages/super-editor/src/tests/toolbar/updateToolbarState.test.js
@@ -40,13 +40,18 @@ describe('updateToolbarState', () => {
   let mockGetQuickFormatList;
   let mockCollectTrackedChanges;
   let mockIsTrackedChangeActionAllowed;
+  let mockFindParentNode;
+  let mockCalculateResolvedParagraphProperties;
 
   beforeEach(async () => {
     vi.clearAllMocks();
 
     mockEditor = {
       state: {
-        selection: { from: 1, to: 1 },
+        selection: { from: 1, to: 1, empty: true },
+        doc: {
+          resolve: vi.fn().mockReturnValue({}),
+        },
       },
       commands: {
         setFieldAnnotationsFontSize: vi.fn(),
@@ -60,6 +65,7 @@ describe('updateToolbarState', () => {
         getDocumentDefaultStyles: vi.fn(() => ({ typeface: 'Arial', fontSizePt: 12 })),
         linkedStyles: [],
         docHiglightColors: new Set(['#ff0000', '#00ff00']),
+        convertedXml: {},
       },
       options: {
         mode: 'docx',
@@ -79,6 +85,13 @@ describe('updateToolbarState', () => {
     const { collectTrackedChanges, isTrackedChangeActionAllowed } = await import(
       '@extensions/track-changes/permission-helpers.js'
     );
+    const helpersModule = await import('@helpers/index.js');
+    mockFindParentNode = helpersModule.findParentNode;
+    mockFindParentNode.mockImplementation(() => vi.fn().mockReturnValue(null));
+    const resolvedPropsModule = await import('@extensions/paragraph/resolvedPropertiesCache.js');
+    mockCalculateResolvedParagraphProperties = vi
+      .spyOn(resolvedPropsModule, 'calculateResolvedParagraphProperties')
+      .mockReturnValue({});
 
     getActiveFormatting.mockImplementation(mockGetActiveFormatting);
     isInTable.mockImplementation(mockIsInTable);
@@ -154,6 +167,7 @@ describe('updateToolbarState', () => {
         setDisabled: vi.fn(),
         defaultLabel: { value: '' },
         allowWithoutEditor: { value: false },
+        active: { value: false },
       },
       {
         name: { value: 'lineHeight' },
@@ -195,6 +209,10 @@ describe('updateToolbarState', () => {
     toolbar.documentMode = 'editing';
   });
 
+  afterEach(() => {
+    mockCalculateResolvedParagraphProperties?.mockRestore?.();
+  });
+
   describe('document mode dropdown sync', () => {
     let documentModeItem;
 
@@ -508,6 +526,79 @@ describe('updateToolbarState', () => {
     expect(fontFamilyItem.activate).not.toHaveBeenCalledWith({ fontFamily: 'Arial' });
   });
 
+  it('falls back to paragraph runProperties font family for empty paragraph with collapsed selection', () => {
+    const paragraphParent = {
+      node: {
+        content: { size: 0 },
+        attrs: { paragraphProperties: {} },
+      },
+      pos: 5,
+    };
+
+    mockFindParentNode.mockImplementation(() => () => paragraphParent);
+    const paragraphFontFamily = 'Fancy Font, serif';
+    mockCalculateResolvedParagraphProperties.mockReturnValue({
+      runProperties: { fontFamily: { 'w:ascii': paragraphFontFamily } },
+    });
+    mockGetActiveFormatting.mockReturnValue([]);
+
+    toolbar.updateToolbarState();
+
+    const fontFamilyItem = toolbar.toolbarItems.find((item) => item.name.value === 'fontFamily');
+    expect(mockCalculateResolvedParagraphProperties).toHaveBeenCalled();
+    expect(fontFamilyItem.activate).toHaveBeenCalledWith({ fontFamily: paragraphFontFamily });
+  });
+
+  it('does not fallback to paragraph font when paragraph already contains text', () => {
+    const paragraphParent = {
+      node: {
+        content: { size: 1 },
+        attrs: { paragraphProperties: {} },
+      },
+      pos: 5,
+    };
+
+    mockFindParentNode.mockImplementation(() => () => paragraphParent);
+    mockCalculateResolvedParagraphProperties.mockReturnValue({
+      runProperties: { fontFamily: { 'w:ascii': 'Never Used' } },
+    });
+    mockGetActiveFormatting.mockReturnValue([]);
+
+    toolbar.updateToolbarState();
+
+    const fontFamilyItem = toolbar.toolbarItems.find((item) => item.name.value === 'fontFamily');
+    expect(fontFamilyItem.activate).not.toHaveBeenCalled();
+  });
+
+  it('keeps linked style font family over paragraph fallback in empty paragraphs', () => {
+    const paragraphParent = {
+      node: {
+        content: { size: 0 },
+        attrs: { paragraphProperties: {} },
+      },
+      pos: 5,
+    };
+
+    mockFindParentNode.mockImplementation(() => () => paragraphParent);
+    mockCalculateResolvedParagraphProperties.mockReturnValue({
+      styleId: 'test-style',
+      runProperties: { fontFamily: { 'w:ascii': 'Paragraph Font, serif' } },
+    });
+    mockEditor.converter.linkedStyles = [
+      {
+        id: 'test-style',
+        definition: { styles: { 'font-family': 'Linked Style Font' } },
+      },
+    ];
+    mockGetActiveFormatting.mockReturnValue([]);
+
+    toolbar.updateToolbarState();
+
+    const fontFamilyItem = toolbar.toolbarItems.find((item) => item.name.value === 'fontFamily');
+    expect(fontFamilyItem.activate).toHaveBeenCalledWith({ fontFamily: 'Linked Style Font' });
+    expect(fontFamilyItem.activate).not.toHaveBeenCalledWith({ fontFamily: 'Paragraph Font, serif' });
+  });
+
   it('should prioritize active mark over linked styles (font size)', () => {
     mockGetActiveFormatting.mockReturnValue([
       { name: 'fontSize', attrs: { fontSize: '20pt' } },