diff --git a/ts_web/elements/wysiwyg/dees-formatting-menu.ts b/ts_web/elements/wysiwyg/dees-formatting-menu.ts
index 14682e3..3755724 100644
--- a/ts_web/elements/wysiwyg/dees-formatting-menu.ts
+++ b/ts_web/elements/wysiwyg/dees-formatting-menu.ts
@@ -162,9 +162,11 @@ export class DeesFormattingMenu extends DeesElement {
   }
 
   public show(position: { x: number; y: number }, callback: (command: string) => void | Promise<void>): void {
+    console.log('FormattingMenu.show called:', { position, visible: this.visible });
     this.position = position;
     this.callback = callback;
     this.visible = true;
+    console.log('FormattingMenu.show - visible set to:', this.visible);
   }
 
   public hide(): void {
diff --git a/ts_web/elements/wysiwyg/dees-input-wysiwyg.ts b/ts_web/elements/wysiwyg/dees-input-wysiwyg.ts
index 18ccb91..23d94f6 100644
--- a/ts_web/elements/wysiwyg/dees-input-wysiwyg.ts
+++ b/ts_web/elements/wysiwyg/dees-input-wysiwyg.ts
@@ -24,6 +24,7 @@ import {
   WysiwygDragDropHandler,
   WysiwygModalManager,
   WysiwygHistory,
+  WysiwygSelection,
   DeesSlashMenu,
   DeesFormattingMenu
 } from './index.js';
@@ -138,11 +139,38 @@ export class DeesInputWysiwyg extends DeesInputBase<string> {
     console.log('Adding selectionchange listener');
     document.addEventListener('selectionchange', this.selectionChangeHandler);
     
+    // Also add listener to our shadow root if supported
+    if (this.shadowRoot && 'addEventListener' in this.shadowRoot) {
+      this.shadowRoot.addEventListener('selectionchange', this.selectionChangeHandler);
+    }
+    
     // Listen for custom selection events from blocks
     this.addEventListener('block-text-selected', (e: CustomEvent) => {
+      console.log('Received block-text-selected event:', e.detail);
+      
       if (!this.slashMenu.visible) {
-        this.selectedText = e.detail.text;
-        this.updateFormattingMenuPosition();
+        if (e.detail.hasSelection && e.detail.text.length > 0) {
+          this.selectedText = e.detail.text;
+          
+          // Use the rect from the event if available
+          if (e.detail.rect) {
+            const coords = {
+              x: e.detail.rect.left + (e.detail.rect.width / 2),
+              y: Math.max(45, e.detail.rect.top - 45)
+            };
+            
+            // Show the formatting menu at the calculated position
+            this.formattingMenu.show(
+              coords,
+              async (command: string) => await this.applyFormat(command)
+            );
+          } else {
+            this.updateFormattingMenuPosition();
+          }
+        } else {
+          // Clear selection
+          this.hideFormattingMenu();
+        }
       }
     });
     
@@ -700,72 +728,157 @@ export class DeesInputWysiwyg extends DeesInputBase<string> {
   }
 
   private handleSelectionChange(): void {
-    // Try to get selection from shadow root first, then fall back to window
-    const shadowSelection = (this.shadowRoot as any).getSelection ? (this.shadowRoot as any).getSelection() : null;
-    const windowSelection = window.getSelection();
-    const editorContent = this.shadowRoot?.querySelector('.editor-content') as HTMLElement;
+    console.log('=== handleSelectionChange called ===');
     
-    // Check both shadow and window selections
-    let selection = shadowSelection;
-    let selectedText = shadowSelection?.toString() || '';
-    
-    // If no shadow selection, check window selection
-    if (!selectedText && windowSelection) {
-      selection = windowSelection;
-      selectedText = windowSelection.toString() || '';
-    }
-    
-    console.log('Selection change:', {
-      hasText: selectedText.length > 0,
-      selectedText: selectedText.substring(0, 50),
-      shadowSelection: !!shadowSelection,
-      windowSelection: !!windowSelection,
-      rangeCount: selection?.rangeCount,
-      editorContent: !!editorContent
-    });
-    
-    if (!selection || selection.rangeCount === 0 || !editorContent) {
-      console.log('No selection or editor content');
+    const selection = window.getSelection();
+    if (!selection || selection.rangeCount === 0) {
+      if (this.formattingMenu.visible) {
+        console.log('No selection, hiding menu');
+        this.hideFormattingMenu();
+      }
       return;
     }
     
-    // If we have selected text, show the formatting menu
-    if (selectedText.length > 0) {
-      console.log('✅ Text selected:', selectedText);
-      
-      if (selectedText !== this.selectedText) {
-        this.selectedText = selectedText;
-        this.updateFormattingMenuPosition();
+    const selectedText = selection.toString().trim();
+    console.log('Selected text:', selectedText);
+    
+    if (selectedText.length === 0) {
+      if (this.formattingMenu.visible) {
+        console.log('No text selected, hiding menu');
+        this.hideFormattingMenu();
       }
-    } else if (this.formattingMenu.visible) {
-      console.log('No text selected, hiding menu');
+      return;
+    }
+    
+    // Get all shadow roots in our component tree
+    const shadowRoots: ShadowRoot[] = [];
+    if (this.shadowRoot) shadowRoots.push(this.shadowRoot);
+    
+    // Find all block shadow roots
+    const blockWrappers = this.shadowRoot?.querySelectorAll('.block-wrapper');
+    console.log('Found block wrappers:', blockWrappers?.length || 0);
+    
+    blockWrappers?.forEach(wrapper => {
+      const blockComponent = wrapper.querySelector('dees-wysiwyg-block');
+      if (blockComponent?.shadowRoot) {
+        shadowRoots.push(blockComponent.shadowRoot);
+      }
+    });
+    
+    console.log('Shadow roots collected:', shadowRoots.length);
+    
+    // Try using getComposedRanges if available
+    let ranges: Range[] | StaticRange[] = [];
+    let selectionInEditor = false;
+    
+    if ('getComposedRanges' in selection && typeof selection.getComposedRanges === 'function') {
+      console.log('Using getComposedRanges with shadow roots');
+      try {
+        // According to MDN, pass shadow roots in options object
+        ranges = selection.getComposedRanges({ shadowRoots });
+        console.log('getComposedRanges returned', ranges.length, 'ranges');
+        
+        if (ranges.length > 0) {
+          const range = ranges[0];
+          // Check if the range is within our editor
+          selectionInEditor = this.isRangeInEditor(range);
+        }
+      } catch (error) {
+        console.warn('getComposedRanges failed:', error);
+      }
+    }
+    
+    // Fallback to regular selection API
+    if (ranges.length === 0 && selection.rangeCount > 0) {
+      console.log('Falling back to getRangeAt');
+      const range = selection.getRangeAt(0);
+      ranges = [range];
+      selectionInEditor = this.isRangeInEditor(range);
+    }
+    
+    console.log('Selection in editor:', selectionInEditor);
+    
+    if (selectionInEditor && selectedText !== this.selectedText) {
+      console.log('✅ Text selected in editor:', selectedText);
+      this.selectedText = selectedText;
+      this.updateFormattingMenuPosition();
+    } else if (!selectionInEditor && this.formattingMenu.visible) {
+      console.log('Selection not in editor, hiding menu');
       this.hideFormattingMenu();
     }
   }
   
+  private isRangeInEditor(range: Range | StaticRange): boolean {
+    // Check if the selection is within one of our blocks
+    const blockWrappers = this.shadowRoot?.querySelectorAll('.block-wrapper');
+    if (!blockWrappers) return false;
+    
+    // Check each block
+    for (let i = 0; i < blockWrappers.length; i++) {
+      const wrapper = blockWrappers[i];
+      const blockComponent = wrapper.querySelector('dees-wysiwyg-block');
+      if (blockComponent?.shadowRoot) {
+        const editableElements = blockComponent.shadowRoot.querySelectorAll('.block, .block.code');
+        for (let j = 0; j < editableElements.length; j++) {
+          const elem = editableElements[j];
+          if (elem) {
+            // For StaticRange, we need to check differently
+            if ('startContainer' in range) {
+              // Check if the range nodes are within this element
+              const startInElement = this.isNodeInElement(range.startContainer, elem);
+              const endInElement = this.isNodeInElement(range.endContainer, elem);
+              
+              if (startInElement || endInElement) {
+                console.log('Selection found in block:', wrapper.getAttribute('data-block-id'));
+                return true;
+              }
+            }
+          }
+        }
+      }
+    }
+    
+    console.log('Selection not in any block. Range:', range);
+    return false;
+  }
+  
+  /**
+   * Check if a node is within an element (handles shadow DOM)
+   */
+  private isNodeInElement(node: Node, element: Element): boolean {
+    let current: Node | null = node;
+    while (current) {
+      if (current === element) return true;
+      // Walk up the tree, including shadow host if in shadow DOM
+      current = current.parentNode || (current as any).host;
+    }
+    return false;
+  }
+  
 
   private updateFormattingMenuPosition(): void {
     console.log('updateFormattingMenuPosition called');
-    const coords = WysiwygFormatting.getSelectionCoordinates(this.shadowRoot as ShadowRoot);
+    
+    // Get all shadow roots
+    const shadowRoots: ShadowRoot[] = [];
+    if (this.shadowRoot) shadowRoots.push(this.shadowRoot);
+    
+    // Find all block shadow roots
+    const blockWrappers = this.shadowRoot?.querySelectorAll('.block-wrapper');
+    blockWrappers?.forEach(wrapper => {
+      const blockComponent = wrapper.querySelector('dees-wysiwyg-block');
+      if (blockComponent?.shadowRoot) {
+        shadowRoots.push(blockComponent.shadowRoot);
+      }
+    });
+    
+    const coords = WysiwygFormatting.getSelectionCoordinates(...shadowRoots);
     console.log('Selection coordinates:', coords);
     
     if (coords) {
-      const container = this.shadowRoot!.querySelector('.wysiwyg-container');
-      if (!container) {
-        console.error('Container not found!');
-        return;
-      }
-      
-      const containerRect = container.getBoundingClientRect();
-      const formattingMenuPosition = {
-        x: coords.x - containerRect.left,
-        y: coords.y - containerRect.top
-      };
-      
-      console.log('Setting menu position:', formattingMenuPosition);
-      // Show the global formatting menu
+      // Show the global formatting menu at absolute coordinates
       this.formattingMenu.show(
-        { x: coords.x, y: coords.y }, // Use absolute coordinates
+        { x: coords.x, y: coords.y },
         async (command: string) => await this.applyFormat(command)
       );
     } else {
@@ -779,33 +892,56 @@ export class DeesInputWysiwyg extends DeesInputBase<string> {
   }
 
   public async applyFormat(command: string): Promise<void> {
-    // Save current selection before applying format
-    const selection = window.getSelection();
-    if (!selection || selection.rangeCount === 0) return;
-
-    // Get the current block
-    const anchorNode = selection.anchorNode;
-    const blockElement = anchorNode?.nodeType === Node.TEXT_NODE 
-      ? anchorNode.parentElement?.closest('.block')
-      : (anchorNode as Element)?.closest('.block');
+    // Get all shadow roots
+    const shadowRoots: ShadowRoot[] = [];
+    if (this.shadowRoot) shadowRoots.push(this.shadowRoot);
     
-    if (!blockElement) return;
-
-    const blockWrapper = blockElement.closest('.block-wrapper');
-    const blockId = blockWrapper?.getAttribute('data-block-id');
-    const block = this.blocks.find(b => b.id === blockId);
-    const blockComponent = blockWrapper?.querySelector('dees-wysiwyg-block') as any;
+    // Find all block shadow roots
+    const blockWrappers = this.shadowRoot?.querySelectorAll('.block-wrapper');
+    blockWrappers?.forEach(wrapper => {
+      const blockComponent = wrapper.querySelector('dees-wysiwyg-block');
+      if (blockComponent?.shadowRoot) {
+        shadowRoots.push(blockComponent.shadowRoot);
+      }
+    });
     
-    if (!block || !blockComponent) return;
+    // Get selection info using Shadow DOM-aware utilities
+    const selectionInfo = WysiwygSelection.getSelectionInfo(...shadowRoots);
+    if (!selectionInfo) return;
+    
+    // Find which block contains the selection
+    let targetBlock: IBlock | undefined;
+    let targetBlockComponent: any;
+    
+    const wrappers = this.shadowRoot!.querySelectorAll('.block-wrapper');
+    for (let i = 0; i < wrappers.length; i++) {
+      const wrapper = wrappers[i];
+      const blockComponent = wrapper.querySelector('dees-wysiwyg-block') as any;
+      if (blockComponent?.shadowRoot) {
+        const block = blockComponent.shadowRoot.querySelector('.block');
+        if (block && (
+          block.contains(selectionInfo.startContainer) || 
+          block.contains(selectionInfo.endContainer)
+        )) {
+          const blockId = wrapper.getAttribute('data-block-id');
+          targetBlock = this.blocks.find(b => b.id === blockId);
+          targetBlockComponent = blockComponent;
+          break;
+        }
+      }
+    }
+    
+    if (!targetBlock || !targetBlockComponent) return;
 
     // Handle link command specially
     if (command === 'link') {
       const url = await this.showLinkDialog();
       if (!url) {
         // User cancelled - restore focus to block
-        blockComponent.focus();
+        targetBlockComponent.focus();
         return;
       }
+      // Apply link format
       WysiwygFormatting.applyFormat(command, url);
     } else {
       // Apply the format
@@ -813,10 +949,10 @@ export class DeesInputWysiwyg extends DeesInputBase<string> {
     }
 
     // Update content after a microtask to ensure DOM is updated
-    await new Promise(resolve => setTimeout(resolve, 0));
+    await new Promise(resolve => setTimeout(resolve, 10));
     
     // Force content update
-    block.content = blockComponent.getContent();
+    targetBlock.content = targetBlockComponent.getContent();
     
     // Update value to persist changes
     this.updateValue();
@@ -825,14 +961,9 @@ export class DeesInputWysiwyg extends DeesInputBase<string> {
     if (command === 'link') {
       this.hideFormattingMenu();
     } else if (this.formattingMenu.visible) {
-      // Update menu position if still showing
+      // Keep selection and update menu position
       this.updateFormattingMenuPosition();
     }
-    
-    // Ensure block still has focus
-    if (document.activeElement !== blockElement) {
-      blockComponent.focus();
-    }
   }
 
   private async showLinkDialog(): Promise<string | null> {
diff --git a/ts_web/elements/wysiwyg/dees-wysiwyg-block.ts b/ts_web/elements/wysiwyg/dees-wysiwyg-block.ts
index b41fb9c..404c211 100644
--- a/ts_web/elements/wysiwyg/dees-wysiwyg-block.ts
+++ b/ts_web/elements/wysiwyg/dees-wysiwyg-block.ts
@@ -315,6 +315,13 @@ export class DeesWysiwygBlock extends DeesElement {
         if (pos !== null) {
           this.lastKnownCursorPosition = pos;
         }
+        
+        // Check for selection after keyboard navigation
+        if (e.shiftKey || ['ArrowLeft', 'ArrowRight', 'ArrowUp', 'ArrowDown'].includes(e.key)) {
+          setTimeout(() => {
+            this.checkForTextSelection();
+          }, 10);
+        }
       });
       
       editableBlock.addEventListener('focus', () => {
@@ -341,6 +348,9 @@ export class DeesWysiwygBlock extends DeesElement {
             this.lastKnownCursorPosition = pos;
             console.log('Cursor position after mouseup:', pos);
           }
+          
+          // Check for text selection
+          this.checkForTextSelection();
         }, 0);
         
         this.handleMouseUp(e);
@@ -778,32 +788,75 @@ export class DeesWysiwygBlock extends DeesElement {
   }
   
   private handleMouseUp(_e: MouseEvent): void {
-    // Check if we have a selection within this block
-    setTimeout(() => {
-      const selection = window.getSelection();
-      if (selection && selection.rangeCount > 0) {
-        const range = selection.getRangeAt(0);
-        
-        // Check if selection is within this block
-        const editableElement = this.block?.type === 'code' 
-          ? this.shadowRoot?.querySelector('.block.code') as HTMLDivElement
-          : this.shadowRoot?.querySelector('.block') as HTMLDivElement;
-        if (editableElement && editableElement.contains(range.commonAncestorContainer)) {
-          const selectedText = selection.toString();
-          if (selectedText.length > 0) {
-            // Dispatch a custom event that can cross shadow DOM boundaries
-            this.dispatchEvent(new CustomEvent('block-text-selected', {
-              detail: { 
-                text: selectedText,
-                blockId: this.block.id,
-                range: range
-              },
-              bubbles: true,
-              composed: true
-            }));
-          }
-        }
-      }
-    }, 10);
+    // Selection check is now handled in the mouseup event listener
+  }
+  
+  /**
+   * Check if there's text selected within this block
+   */
+  private checkForTextSelection(): void {
+    const editableElement = this.block?.type === 'code' 
+      ? this.shadowRoot?.querySelector('.block.code') as HTMLDivElement
+      : this.shadowRoot?.querySelector('.block') as HTMLDivElement;
+    if (!editableElement) return;
+    
+    const selection = window.getSelection();
+    if (!selection || selection.rangeCount === 0) {
+      // Dispatch event to clear selection
+      this.dispatchEvent(new CustomEvent('block-text-selected', {
+        detail: {
+          text: '',
+          blockId: this.block.id,
+          hasSelection: false
+        },
+        bubbles: true,
+        composed: true
+      }));
+      return;
+    }
+    
+    const selectedText = selection.toString().trim();
+    
+    // Only proceed if we have selected text
+    if (selectedText.length === 0) {
+      // Dispatch event to clear selection
+      this.dispatchEvent(new CustomEvent('block-text-selected', {
+        detail: {
+          text: '',
+          blockId: this.block.id,
+          hasSelection: false
+        },
+        bubbles: true,
+        composed: true
+      }));
+      return;
+    }
+    
+    // Check if the selection is within this block
+    const range = selection.getRangeAt(0);
+    
+    // Check if both start and end are within our editable element
+    const startInBlock = editableElement.contains(range.startContainer);
+    const endInBlock = editableElement.contains(range.endContainer);
+    
+    if (startInBlock && endInBlock) {
+      console.log('Block detected text selection:', selectedText);
+      
+      // Get the bounding rect of the selection
+      const rect = range.getBoundingClientRect();
+      
+      // Dispatch event to parent with selection details
+      this.dispatchEvent(new CustomEvent('block-text-selected', {
+        detail: {
+          text: selectedText,
+          blockId: this.block.id,
+          range: range,
+          rect: rect,
+          hasSelection: true
+        },
+        bubbles: true,
+        composed: true
+      }));
+    }
   }
 }
\ No newline at end of file
diff --git a/ts_web/elements/wysiwyg/wysiwyg.formatting.ts b/ts_web/elements/wysiwyg/wysiwyg.formatting.ts
index 46f136d..7aad5d6 100644
--- a/ts_web/elements/wysiwyg/wysiwyg.formatting.ts
+++ b/ts_web/elements/wysiwyg/wysiwyg.formatting.ts
@@ -143,11 +143,9 @@ export class WysiwygFormatting {
     }
   }
 
-  static getSelectionCoordinates(shadowRoot?: ShadowRoot): { x: number, y: number } | null {
+  static getSelectionCoordinates(...shadowRoots: ShadowRoot[]): { x: number, y: number } | null {
     // Get selection info using the new utility that handles Shadow DOM
-    const selectionInfo = shadowRoot 
-      ? WysiwygSelection.getSelectionInfo(shadowRoot)
-      : WysiwygSelection.getSelectionInfo();
+    const selectionInfo = WysiwygSelection.getSelectionInfo(...shadowRoots);
     
     console.log('getSelectionCoordinates - selectionInfo:', selectionInfo);
     
@@ -162,8 +160,29 @@ export class WysiwygFormatting {
     
     console.log('Range rect:', rect);
     
-    if (rect.width === 0) {
-      console.log('Rect width is 0');
+    if (rect.width === 0 && rect.height === 0) {
+      console.log('Rect width and height are 0, trying different approach');
+      // Sometimes the rect is collapsed, let's try getting the caret position
+      if ('caretPositionFromPoint' in document) {
+        const selection = window.getSelection();
+        if (selection && selection.rangeCount > 0) {
+          const range = selection.getRangeAt(0);
+          const tempSpan = document.createElement('span');
+          tempSpan.textContent = '\u200B'; // Zero-width space
+          range.insertNode(tempSpan);
+          const spanRect = tempSpan.getBoundingClientRect();
+          tempSpan.remove();
+          
+          if (spanRect.width > 0 || spanRect.height > 0) {
+            const coords = {
+              x: spanRect.left,
+              y: Math.max(45, spanRect.top - 45)
+            };
+            console.log('Used span trick for coords:', coords);
+            return coords;
+          }
+        }
+      }
       return null;
     }
 
diff --git a/ts_web/elements/wysiwyg/wysiwyg.selection.ts b/ts_web/elements/wysiwyg/wysiwyg.selection.ts
index 414ebc7..3948b0b 100644
--- a/ts_web/elements/wysiwyg/wysiwyg.selection.ts
+++ b/ts_web/elements/wysiwyg/wysiwyg.selection.ts
@@ -20,13 +20,16 @@ export class WysiwygSelection {
    */
   static getSelectionInfo(...shadowRoots: ShadowRoot[]): SelectionInfo | null {
     const selection = window.getSelection();
+    console.log('WysiwygSelection.getSelectionInfo - selection:', selection, 'rangeCount:', selection?.rangeCount);
     if (!selection) return null;
 
     // Try using getComposedRanges if available (better Shadow DOM support)
     if ('getComposedRanges' in selection && typeof selection.getComposedRanges === 'function') {
+      console.log('Using getComposedRanges with', shadowRoots.length, 'shadow roots');
       try {
         // Pass shadow roots in the correct format as per MDN
         const ranges = selection.getComposedRanges({ shadowRoots });
+        console.log('getComposedRanges returned', ranges.length, 'ranges');
         if (ranges.length > 0) {
           const range = ranges[0];
           return {
@@ -40,6 +43,8 @@ export class WysiwygSelection {
       } catch (error) {
         console.warn('getComposedRanges failed, falling back to getRangeAt:', error);
       }
+    } else {
+      console.log('getComposedRanges not available, using fallback');
     }
 
     // Fallback to traditional selection API