diff --git a/DocumentOperator.Infrastructure/Services/PdfProcessing/DevExpressPdfProcessor.cs b/DocumentOperator.Infrastructure/Services/PdfProcessing/DevExpressPdfProcessor.cs
index 7bfb97e..59df11c 100644
--- a/DocumentOperator.Infrastructure/Services/PdfProcessing/DevExpressPdfProcessor.cs
+++ b/DocumentOperator.Infrastructure/Services/PdfProcessing/DevExpressPdfProcessor.cs
@@ -390,6 +390,247 @@ public class DevExpressPdfProcessor : IPdfProcessor
 
     #endregion
 
+    #region PDF Annotation
+
+    /// <summary>
+    /// Adds an annotation to a PDF document at the specified page and rectangle.
+    /// </summary>
+    public async Task<byte[]> AddAnnotationAsync(
+        Stream pdfStream,
+        Domain.Models.ValueObjects.AnnotationType annotationType,
+        int pageNumber,
+        (double X1, double Y1, double X2, double Y2) rectangle,
+        string? content = null,
+        string? author = null,
+        string? color = null,
+        Domain.Models.ValueObjects.TextMarkupStyle? textMarkupStyle = null)
+    {
+        // 1. Input validation
+        ArgumentNullException.ThrowIfNull(pdfStream, nameof(pdfStream));
+        
+        if (pdfStream.Length == 0)
+            throw new BadRequestException("PDF stream cannot be empty");
+
+        if (pdfStream.Position != 0)
+            throw new BadRequestException($"PDF stream must be at position 0 (current position: {pdfStream.Position})");
+
+        if (pageNumber < 1)
+            throw new BadRequestException($"Page number must be >= 1 (provided: {pageNumber})");
+
+        // Validate content requirement
+        if (annotationType is Domain.Models.ValueObjects.AnnotationType.FreeText 
+            or Domain.Models.ValueObjects.AnnotationType.StickyNote)
+        {
+            if (string.IsNullOrWhiteSpace(content))
+                throw new BadRequestException($"{annotationType} annotation requires content");
+        }
+
+        // Validate TextMarkup style requirement
+        if (annotationType == Domain.Models.ValueObjects.AnnotationType.TextMarkup && textMarkupStyle == null)
+            throw new BadRequestException("TextMarkup annotation requires textMarkupStyle parameter");
+
+        byte[] annotatedPdfBytes;
+
+        try
+        {
+            // 2. Load PDF
+            using var processor = new PdfDocumentProcessor();
+            processor.LoadDocument(pdfStream);
+
+            // 3. Validate page number
+            int pageCount = processor.Document.Pages.Count;
+            if (pageNumber > pageCount)
+                throw new BadRequestException($"Page number {pageNumber} exceeds document page count ({pageCount})");
+
+            // 4. Get page facade (zero-based index)
+            var pageFacade = processor.DocumentFacade.Pages[pageNumber - 1];
+
+            // 5. Create annotation rectangle
+            var pdfRectangle = new PdfRectangle(rectangle.X1, rectangle.Y1, rectangle.X2, rectangle.Y2);
+
+            // 6. Parse color (default to yellow for highlights, red for others)
+            PdfRGBColor annotationColor = ParseColor(color) ?? (annotationType == Domain.Models.ValueObjects.AnnotationType.TextMarkup 
+                ? new PdfRGBColor(1.0, 1.0, 0) // Yellow
+                : new PdfRGBColor(1.0, 0, 0)); // Red
+
+            // 7. Add annotation based on type
+            switch (annotationType)
+            {
+                case Domain.Models.ValueObjects.AnnotationType.TextMarkup:
+                    AddTextMarkupAnnotation(pageFacade, pdfRectangle, textMarkupStyle!.Value, content, author, annotationColor);
+                    break;
+
+                case Domain.Models.ValueObjects.AnnotationType.FreeText:
+                    AddFreeTextAnnotation(pageFacade, pdfRectangle, content!, author, annotationColor);
+                    break;
+
+                case Domain.Models.ValueObjects.AnnotationType.StickyNote:
+                    AddStickyNoteAnnotation(pageFacade, pdfRectangle, content!, author, annotationColor);
+                    break;
+
+                case Domain.Models.ValueObjects.AnnotationType.Circle:
+                    AddCircleAnnotation(pageFacade, pdfRectangle, content, author, annotationColor);
+                    break;
+
+                case Domain.Models.ValueObjects.AnnotationType.Square:
+                    AddSquareAnnotation(pageFacade, pdfRectangle, content, author, annotationColor);
+                    break;
+
+                default:
+                    throw new BadRequestException($"Unsupported annotation type: {annotationType}");
+            }
+
+            // 8. Save annotated PDF
+            using var outputStream = new MemoryStream();
+            processor.SaveDocument(outputStream);
+            annotatedPdfBytes = outputStream.ToArray();
+        }
+        catch (BadRequestException)
+        {
+            throw; // Re-throw our own exceptions
+        }
+        catch (Exception ex)
+        {
+            throw new BadRequestException($"Failed to add annotation: {ex.Message}");
+        }
+
+        return await Task.FromResult(annotatedPdfBytes);
+    }
+
+    private void AddTextMarkupAnnotation(
+        PdfPageFacade pageFacade,
+        PdfRectangle rectangle,
+        Domain.Models.ValueObjects.TextMarkupStyle style,
+        string? content,
+        string? author,
+        PdfRGBColor color)
+    {
+        // Map our enum to DevExpress enum
+        var devExpressStyle = style switch
+        {
+            Domain.Models.ValueObjects.TextMarkupStyle.Highlight => PdfTextMarkupAnnotationType.Highlight,
+            Domain.Models.ValueObjects.TextMarkupStyle.Underline => PdfTextMarkupAnnotationType.Underline,
+            Domain.Models.ValueObjects.TextMarkupStyle.Strikeout => PdfTextMarkupAnnotationType.StrikeOut,
+            _ => throw new BadRequestException($"Unsupported text markup style: {style}")
+        };
+
+        var annotation = pageFacade.AddTextMarkupAnnotation(rectangle, devExpressStyle);
+        
+        if (annotation != null)
+        {
+            annotation.Color = color;
+            if (!string.IsNullOrWhiteSpace(author))
+                annotation.Author = author;
+            if (!string.IsNullOrWhiteSpace(content))
+                annotation.Contents = content;
+        }
+    }
+
+    private void AddFreeTextAnnotation(
+        PdfPageFacade pageFacade,
+        PdfRectangle rectangle,
+        string content,
+        string? author,
+        PdfRGBColor color)
+    {
+        var annotation = pageFacade.AddFreeTextAnnotation(rectangle, content);
+        
+        if (annotation != null)
+        {
+            annotation.Color = color;
+            if (!string.IsNullOrWhiteSpace(author))
+                annotation.Author = author;
+        }
+    }
+
+    private void AddStickyNoteAnnotation(
+        PdfPageFacade pageFacade,
+        PdfRectangle rectangle,
+        string content,
+        string? author,
+        PdfRGBColor color)
+    {
+        // Sticky note uses a point (top-left corner of rectangle)
+        var point = new PdfPoint(rectangle.Left, rectangle.Top);
+        var annotation = pageFacade.AddTextAnnotation(point);
+        
+        if (annotation != null)
+        {
+            annotation.Color = color;
+            annotation.Contents = content;
+            if (!string.IsNullOrWhiteSpace(author))
+                annotation.Author = author;
+        }
+    }
+
+    private void AddCircleAnnotation(
+        PdfPageFacade pageFacade,
+        PdfRectangle rectangle,
+        string? content,
+        string? author,
+        PdfRGBColor color)
+    {
+        var annotation = pageFacade.AddCircleAnnotation(rectangle);
+        
+        if (annotation != null)
+        {
+            annotation.Color = color;
+            if (!string.IsNullOrWhiteSpace(author))
+                annotation.Author = author;
+            if (!string.IsNullOrWhiteSpace(content))
+                annotation.Contents = content;
+        }
+    }
+
+    private void AddSquareAnnotation(
+        PdfPageFacade pageFacade,
+        PdfRectangle rectangle,
+        string? content,
+        string? author,
+        PdfRGBColor color)
+    {
+        var annotation = pageFacade.AddSquareAnnotation(rectangle);
+        
+        if (annotation != null)
+        {
+            annotation.Color = color;
+            if (!string.IsNullOrWhiteSpace(author))
+                annotation.Author = author;
+            if (!string.IsNullOrWhiteSpace(content))
+                annotation.Contents = content;
+        }
+    }
+
+    /// <summary>
+    /// Parses hex color string (e.g., "FF0000" for red) to PdfRGBColor
+    /// </summary>
+    private PdfRGBColor? ParseColor(string? hexColor)
+    {
+        if (string.IsNullOrWhiteSpace(hexColor))
+            return null;
+
+        try
+        {
+            // Remove '#' if present
+            hexColor = hexColor.TrimStart('#');
+
+            if (hexColor.Length != 6)
+                throw new BadRequestException($"Color must be 6-digit hex (e.g., 'FF0000'), got: '{hexColor}'");
+
+            int r = Convert.ToInt32(hexColor.Substring(0, 2), 16);
+            int g = Convert.ToInt32(hexColor.Substring(2, 2), 16);
+            int b = Convert.ToInt32(hexColor.Substring(4, 2), 16);
+
+            return new PdfRGBColor(r / 255.0, g / 255.0, b / 255.0);
+        }
+        catch (Exception ex)
+        {
+            throw new BadRequestException($"Invalid color format: '{hexColor}'. Expected 6-digit hex (e.g., 'FF0000'). Error: {ex.Message}");
+        }
+    }
+
+    #endregion
+
     #region Private Helpers
 
     /// <summary>