diff --git a/app/javascript/src/styles/specific/posts.scss b/app/javascript/src/styles/specific/posts.scss
index fba8ce4d4..628d2a10b 100644
--- a/app/javascript/src/styles/specific/posts.scss
+++ b/app/javascript/src/styles/specific/posts.scss
@@ -159,6 +159,7 @@ div#c-posts {
 
     .image-container {
       margin: 1em 0 0.5em;
+      image-orientation: from-image;
 
       &.danbirthday::before {
         content: "";
diff --git a/app/logical/media_file/image.rb b/app/logical/media_file/image.rb
index 1d3c563c3..9d77c3e33 100644
--- a/app/logical/media_file/image.rb
+++ b/app/logical/media_file/image.rb
@@ -7,15 +7,27 @@ class MediaFile::Image < MediaFile
   JPEG_OPTIONS = { Q: 90, background: 255, strip: true, interlace: true, optimize_coding: true }
 
   # http://jcupitt.github.io/libvips/API/current/libvips-resample.html#vips-thumbnail
-  THUMBNAIL_OPTIONS = { size: :down, linear: false, no_rotate: true }
-  CROP_OPTIONS = { crop: :attention, linear: false, no_rotate: true }
+  THUMBNAIL_OPTIONS = { size: :down, linear: false }
+  CROP_OPTIONS = { crop: :attention, linear: false }
 
   def dimensions
-    image.size
+    [width, height]
   rescue Vips::Error
     [0, 0]
   end
 
+  def width
+    is_rotated? ? image.height : image.width
+  rescue Vips::Error
+    0
+  end
+
+  def height
+    is_rotated? ? image.width : image.height
+  rescue Vips::Error
+    0
+  end
+
   def is_corrupt?
     image.stats
     false
@@ -69,6 +81,11 @@ class MediaFile::Image < MediaFile
     file_ext == :png && metadata.fetch("PNG:AnimationFrames", 1) > 1
   end
 
+  # https://exiftool.org/TagNames/EXIF.html
+  def is_rotated?
+    metadata["IFD0:Orientation"].in?(["Rotate 90 CW", "Rotate 270 CW"])
+  end
+
   # @return [Vips::Image] the Vips image object for the file
   def image
     Vips::Image.new_from_file(file.path, fail: true)
diff --git a/app/models/post.rb b/app/models/post.rb
index 4b70f75fb..b4d13b9c2 100644
--- a/app/models/post.rb
+++ b/app/models/post.rb
@@ -1348,6 +1348,20 @@ class Post < ApplicationRecord
         media_file = MediaFile.open(file, frame_data: pixiv_ugoira_frame_data&.data.to_a)
         UploadService::Utils.process_resizes(self, nil, id, media_file: media_file)
 
+        update!(
+          image_width: media_file.width,
+          image_height: media_file.height,
+          file_size: media_file.file_size,
+          file_ext: media_file.file_ext,
+        )
+
+        media_asset.update!(
+          image_width: media_file.width,
+          image_height: media_file.height,
+          file_size: media_file.file_size,
+          file_ext: media_file.file_ext,
+        )
+
         purge_cached_urls!
         update_iqdb
 
diff --git a/test/files/test-rotation-180.jpg b/test/files/test-rotation-180.jpg
new file mode 100644
index 000000000..63cd9c50b
Binary files /dev/null and b/test/files/test-rotation-180.jpg differ
diff --git a/test/files/test-rotation-270cw.jpg b/test/files/test-rotation-270cw.jpg
new file mode 100644
index 000000000..7939638e8
Binary files /dev/null and b/test/files/test-rotation-270cw.jpg differ
diff --git a/test/functional/post_regenerations_controller_test.rb b/test/functional/post_regenerations_controller_test.rb
index 75a34670f..443fbe047 100644
--- a/test/functional/post_regenerations_controller_test.rb
+++ b/test/functional/post_regenerations_controller_test.rb
@@ -58,6 +58,20 @@ class PostRegenerationsControllerTest < ActionDispatch::IntegrationTest
           assert_equal("post_regenerate", ModAction.last.category)
           assert_equal("<@#{@mod.name}> regenerated image samples for post ##{@post.id}", ModAction.last.description)
         end
+
+        should "fix the width and height of exif-rotated images" do
+          @upload = assert_successful_upload("test/files/test-rotation-90cw.jpg", user: @mod)
+          @post = @upload.post
+
+          post_auth post_regenerations_path, @mod, params: { post_id: @post.id }
+          perform_enqueued_jobs
+          @post.reload
+
+          assert_equal(96, @post.image_width)
+          assert_equal(128, @post.image_height)
+          assert_equal(96, @post.media_asset.image_width)
+          assert_equal(128, @post.media_asset.image_height)
+        end
       end
     end
   end
diff --git a/test/unit/media_file_test.rb b/test/unit/media_file_test.rb
index 021df68cb..6d0650332 100644
--- a/test/unit/media_file_test.rb
+++ b/test/unit/media_file_test.rb
@@ -323,4 +323,40 @@ class MediaFileTest < ActiveSupport::TestCase
       assert_equal([120, 150], @preview.dimensions)
     end
   end
+
+  context "an image that is rotated 90 degrees clockwise" do
+    should "have the correct dimensions" do
+      @file = MediaFile.open("test/files/test-rotation-90cw.jpg")
+      assert_equal([96, 128], @file.dimensions)
+    end
+
+    should "generate a rotated thumbnail" do
+      @file = MediaFile.open("test/files/test-rotation-90cw.jpg")
+      assert_equal([48, 64], @file.preview(64, 64).dimensions)
+    end
+  end
+
+  context "an image that is rotated 270 degrees clockwise" do
+    should "have the correct dimensions" do
+      @file = MediaFile.open("test/files/test-rotation-270cw.jpg")
+      assert_equal([100, 66], @file.dimensions)
+    end
+
+    should "generate a rotated thumbnail" do
+      @file = MediaFile.open("test/files/test-rotation-270cw.jpg")
+      assert_equal([50, 33], @file.preview(50, 50).dimensions)
+    end
+  end
+
+  context "an image that is rotated 180 degrees" do
+    should "have the correct dimensions" do
+      @file = MediaFile.open("test/files/test-rotation-180.jpg")
+      assert_equal([66, 100], @file.dimensions)
+    end
+
+    should "generate a rotated thumbnail" do
+      @file = MediaFile.open("test/files/test-rotation-180.jpg")
+      assert_equal([33, 50], @file.preview(50, 50).dimensions)
+    end
+  end
 end