diff --git a/ElementX/Sources/Services/Media/MediaUploadingPreprocessor.swift b/ElementX/Sources/Services/Media/MediaUploadingPreprocessor.swift
index 0f967d8a5d..9a9b0bcefc 100644
--- a/ElementX/Sources/Services/Media/MediaUploadingPreprocessor.swift
+++ b/ElementX/Sources/Services/Media/MediaUploadingPreprocessor.swift
@@ -449,10 +449,22 @@ struct MediaUploadingPreprocessor {
 private extension CGImageSource {
     var size: CGSize? {
         guard let properties = CGImageSourceCopyPropertiesAtIndex(self, 0, nil) as? [NSString: Any],
-              let width = properties[kCGImagePropertyPixelWidth] as? Int,
-              let height = properties[kCGImagePropertyPixelHeight] as? Int else {
+              var width = properties[kCGImagePropertyPixelWidth] as? Int,
+              var height = properties[kCGImagePropertyPixelHeight] as? Int else {
             return nil
         }
+        
+        // Make sure the width and height are the correct way around if an orientation is set.
+        if let orientationValue = properties[kCGImagePropertyOrientation] as? UInt32,
+           let orientation = CGImagePropertyOrientation(rawValue: orientationValue) {
+            switch orientation {
+            case .up, .down, .upMirrored, .downMirrored:
+                break
+            case .left, .right, .leftMirrored, .rightMirrored:
+                swap(&width, &height)
+            }
+        }
+        
         return CGSize(width: width, height: height)
     }
 }
diff --git a/UnitTests/Resources/Media/test_rotated_image.jpg b/UnitTests/Resources/Media/test_rotated_image.jpg
new file mode 100644
index 0000000000..6169c3717d
--- /dev/null
+++ b/UnitTests/Resources/Media/test_rotated_image.jpg
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:094ceac734f4461ae9f1c47eae58c13270da6f407718b12e3142cac3dc0b38a7
+size 1735894
diff --git a/UnitTests/Sources/MediaUploadingPreprocessorTests.swift b/UnitTests/Sources/MediaUploadingPreprocessorTests.swift
index 7438c3a84c..a9aa74bd59 100644
--- a/UnitTests/Sources/MediaUploadingPreprocessorTests.swift
+++ b/UnitTests/Sources/MediaUploadingPreprocessorTests.swift
@@ -422,6 +422,46 @@ final class MediaUploadingPreprocessorTests: XCTestCase {
         XCTAssertEqual(optimizedImageInfo.height, 498)
     }
     
+    func testRotatedImageProcessing() async {
+        guard let url = Bundle(for: Self.self).url(forResource: "test_rotated_image.jpg", withExtension: nil) else {
+            XCTFail("Failed retrieving test asset")
+            return
+        }
+        
+        guard case let .success(result) = await mediaUploadingPreprocessor.processMedia(at: url),
+              case let .image(convertedImageURL, thumbnailURL, imageInfo) = result else {
+            XCTFail("Failed processing asset")
+            return
+        }
+        
+        compare(originalImageAt: url, toConvertedImageAt: convertedImageURL, withThumbnailAt: thumbnailURL)
+        
+        // Check resulting image info
+        XCTAssertEqual(imageInfo.mimetype, "image/jpeg")
+        XCTAssertEqual(imageInfo.width, 2848)
+        XCTAssertEqual(imageInfo.height, 4272)
+        
+        XCTAssertNotNil(imageInfo.thumbnailInfo)
+        XCTAssertEqual(imageInfo.thumbnailInfo?.width, 533)
+        XCTAssertEqual(imageInfo.thumbnailInfo?.height, 800)
+        
+        // Repeat with optimised media setting
+        appSettings.optimizeMediaUploads = true
+        
+        guard case let .success(optimizedResult) = await mediaUploadingPreprocessor.processMedia(at: url),
+              case let .image(optimizedImageURL, thumbnailURL, optimizedImageInfo) = optimizedResult else {
+            XCTFail("Failed processing asset")
+            return
+        }
+        
+        compare(originalImageAt: url, toConvertedImageAt: optimizedImageURL, withThumbnailAt: thumbnailURL)
+        
+        // Check optimised image info
+        XCTAssertEqual(optimizedImageInfo.mimetype, "image/jpeg")
+        XCTAssertEqual(optimizedImageInfo.width, 1365)
+        XCTAssertEqual(optimizedImageInfo.height, 2048)
+    }
+    
     // MARK: - Private
     
     private func compare(originalImageAt originalImageURL: URL, toConvertedImageAt convertedImageURL: URL, withThumbnailAt thumbnailURL: URL) {