Drawing an upright stamp annotation on a rotated page
When using a custom appearance stream generator to draw a stamp annotation, you’ll have to take care of the rotation offset of the page when drawing the image.
Here’s sample code demonstrating the counter-rotation:
func addUprightStampAnnotation () {    // We need to fetch the `pageInfo` for the page in which the stamp annotation needs to be drawn.    let pageInfo = document.pageInfoForPage(at: 0)
    // Here, we get the rotation of the page and convert it to radians.    let rotation = CGFloat((pageInfo!.rotationOffset.rawValue + pageInfo!.savedRotation.rawValue) % 360) * CGFloat.pi / 180
    let image: UIImage = UIImage.init(named: "stamp-image")!    let stampAnnotation = StampAnnotation()    stampAnnotation.boundingBox = CGRect(x: 200, y: 200, width: 50, height: 50)
    let appearanceStreamGenerator = FileAppearanceStreamGenerator(fileURL: URL(fileURLWithPath: ""))    appearanceStreamGenerator.drawingBlock = { context in        var transform = CGAffineTransform.identity        // First, translate and go to the center of the stamp annotation.        transform = transform.translatedBy(x: stampAnnotation.boundingBox.origin.x + (stampAnnotation.boundingBox.size.width / 2),                                           y: stampAnnotation.boundingBox.origin.y + (stampAnnotation.boundingBox.size.height / 2))        // Now, rotate the context in the opposite direction of the page rotation.        transform = transform.rotated(by: -1 * rotation)        // Translate back to origin.        transform = transform.translatedBy(x: -1 * (stampAnnotation.boundingBox.origin.x + (stampAnnotation.boundingBox.size.width / 2)),                                           y: -1 * (stampAnnotation.boundingBox.origin.y + (stampAnnotation.boundingBox.size.height / 2)))        context.concatenate(transform)        // Draw the image now.        context.draw(image.cgImage!, in: stampAnnotation.boundingBox)    }    stampAnnotation.appearanceStreamGenerator = appearanceStreamGenerator    document.add(annotations: [stampAnnotation])}- (void)addUprightStampAnnotation {    PSPDFDocument *document;    // We need to fetch the `pageInfo` for the page in which the stamp annotation needs to be drawn.    PSPDFPageInfo *pageInfo = [document pageInfoForPageAtIndex:0];
    // Here, we get the rotation of the page and convert it to radians.    CGFloat rotationInDegrees =  (CGFloat)pageInfo.rotationOffset + (CGFloat)pageInfo.savedRotation;    CGFloat rotation = rotationInDegrees * M_PI / 180;
    UIImage *image = [UIImage imageNamed:@"stamp-image"];    PSPDFStampAnnotation *stampAnnotation = [[PSPDFStampAnnotation alloc] init];    stampAnnotation.boundingBox = CGRectMake(200, 200, 50, 50);
    PSPDFFileAppearanceStreamGenerator *appearanceStreamGenerator = [[PSPDFFileAppearanceStreamGenerator alloc] initWithFileURL:[NSURL new]];    [appearanceStreamGenerator setDrawingBlock:^(CGContextRef context) {        CGAffineTransform transform = CGAffineTransformIdentity;
       // First, translate and go to the center of the stamp annotation.        transform = CGAffineTransformTranslate(transform,                                               stampAnnotation.boundingBox.origin.x + (stampAnnotation.boundingBox.size.width / 2),                                               stampAnnotation.boundingBox.origin.y + (stampAnnotation.boundingBox.size.height / 2));
        // Now, rotate the context in the opposite direction of the page rotation.        transform = CGAffineTransformRotate(transform, -1 * rotation);
        // Translate back to origin.        transform = CGAffineTransformTranslate(transform,                                               -1 * (stampAnnotation.boundingBox.origin.x + (stampAnnotation.boundingBox.size.width / 2)),                                               -1 * (stampAnnotation.boundingBox.origin.y + (stampAnnotation.boundingBox.size.height / 2)));
        CGContextConcatCTM(context, transform);
        // Draw the image now.        CGContextDrawImage(context, stampAnnotation.boundingBox, image.CGImage);    }];
    stampAnnotation.appearanceStreamGenerator = appearanceStreamGenerator;    [document addAnnotations:@[stampAnnotation] options:nil];}