diff --git a/inc/Service/Media/LibMagickMediaHandler.php b/inc/Service/Media/LibMagickMediaHandler.php
index 054416bb..14b3b076 100644
--- a/inc/Service/Media/LibMagickMediaHandler.php
+++ b/inc/Service/Media/LibMagickMediaHandler.php
@@ -67,8 +67,7 @@ class LibMagickMediaHandler implements MediaHandler {
 	/**
 	 * @return bool Returns if width and height were swapped.
 	 */
-	private static function adjustOrientation(\Imagick $imagick) {
-		$orientation = $imagick->getImageOrientation();
+	private static function adjustOrientation(\Imagick $imagick, int $orientation): void {
 		$degrees = self::degreesFromOrientation($orientation);
 		$flipped = self::isFlippedFromOrientation($orientation);
 
@@ -81,7 +80,6 @@ class LibMagickMediaHandler implements MediaHandler {
 		if ($flipped) {
 			$imagick->flopImage();
 		}
-		return $degrees !== 0 && $degrees !== 180;
 	}
 
 	private function generateThumbImpl(
@@ -219,15 +217,23 @@ class LibMagickMediaHandler implements MediaHandler {
 		// Open it as the supplied mime type.
 		$imagick = new \Imagick("$ext:$path");
 
-		$width = $imagick->getImageWidth();
-		$height = $imagick->getImageHeight();
+		$orientation = $imagick->getImageOrientation();
 
-		if ($width > $this->image_max_width || $height > $this->image_max_height) {
+		if (self::isFlippedFromOrientation($orientation)) {
+			$width = $imagick->getImageHeight();
+			$height = $imagick->getImageWidth();
+		} else {
+			$width = $imagick->getImageWidth();
+			$height = $imagick->getImageHeight();
+		}
+
+		if ($width > $this->image_max_width && $height > $this->image_max_height) {
+			// Too big even if rotated.
 			$imagick->clear();
 			throw new MediaException("Image too big", MediaException::ERR_IMAGE_TOO_LARGE);
 		}
 
-		return [ $imagick, $file_path, $file_mime, $file_kind ];
+		return [ $imagick, $file_path, $file_mime, $file_kind, $width, $height, $orientation ];
 	}
 
 	public function closeHandle(mixed $handle) {
@@ -241,10 +247,7 @@ class LibMagickMediaHandler implements MediaHandler {
 		int $max_width,
 		int $max_height
 	): ThumbGenerationResult {
-		list($imagick, $source_file_path, $source_file_mime, $source_file_kind) = $handle;
-
-		$width = $imagick->getImageWidth();
-		$height = $imagick->getImageHeight();
+		list($imagick, $source_file_path, $source_file_mime, $source_file_kind, $width, $height, $orientation) = $handle;
 
 		if (!$this->strip_metadata && $width <= $max_width && $height <= $max_height) {
 			$out_path = $preferred_out_file_basepath . '.' . Metadata\mime_to_ext($source_file_mime);
@@ -258,12 +261,7 @@ class LibMagickMediaHandler implements MediaHandler {
 				$max_height
 			);
 		} else {
-			$swap = self::adjustOrientation($imagick);
-			if ($swap) {
-				$tmp = $width;
-				$width = $height;
-				$height = $tmp;
-			}
+			self::adjustOrientation($imagick, $orientation);
 
 			return self::generateThumbImpl(
 				$imagick,
@@ -286,10 +284,7 @@ class LibMagickMediaHandler implements MediaHandler {
 		int $thumb_max_width,
 		int $thumb_max_height
 	): MediaInstallResult {
-		list($imagick, $media_file_path, $media_file_mime, $media_file_kind) = $handle;
-
-		$width = $imagick->getImageWidth();
-		$height = $imagick->getImageHeight();
+		list($imagick, $media_file_path, $media_file_mime, $media_file_kind, $width, $height, $orientation) = $handle;
 
 		if (!$this->strip_metadata) {
 			$media_out_path = $media_preferred_out_file_basepath . '.' . Metadata\mime_to_ext($media_file_mime);
@@ -304,12 +299,7 @@ class LibMagickMediaHandler implements MediaHandler {
 
 				$thumb = new ThumbGenerationResult($thumb_out_path, $media_file_mime, $width, $height);
 			} else {
-				$swap = self::adjustOrientation($imagick);
-				if ($swap) {
-					$tmp = $width;
-					$width = $height;
-					$height = $tmp;
-				}
+				self::adjustOrientation($imagick, $orientation);
 
 				$thumb = self::generateThumbImpl(
 					$imagick,
@@ -324,12 +314,7 @@ class LibMagickMediaHandler implements MediaHandler {
 			}
 			return new MediaInstallResult($thumb, $media_out_path);
 		} else {
-			$swap = self::adjustOrientation($imagick);
-			if ($swap) {
-				$tmp = $width;
-				$width = $height;
-				$height = $tmp;
-			}
+			self::adjustOrientation($imagick, $orientation);
 
 			// Backup the color profile, then re-apply it.
 			$profiles = $imagick->getImageProfiles('icc', true);