diff --git a/app/models/media_asset.rb b/app/models/media_asset.rb
index 4f0b65f24..b9e9c7ca2 100644
--- a/app/models/media_asset.rb
+++ b/app/models/media_asset.rb
@@ -30,4 +30,48 @@ class MediaAsset < ApplicationRecord
   def is_animated_png?
     file_ext == "png" && metadata.fetch("PNG:AnimationFrames", 1) > 1
   end
-end
\ No newline at end of file
+
+  # @see https://exiftool.org/TagNames/JPEG.html
+  # @see https://exiftool.org/TagNames/PNG.html
+  # @see https://danbooru.donmai.us/posts?tags=exif:File:ColorComponents=1
+  # @see https://danbooru.donmai.us/posts?tags=exif:PNG:ColorType=Grayscale
+  def is_greyscale?
+    metadata["File:ColorComponents"] == 1 ||
+    metadata["PNG:ColorType"] == "Grayscale" ||
+    metadata["PNG:ColorType"] == "Grayscale with Alpha"
+
+    # Not always accurate:
+    # metadata["ICC-header:ColorSpaceData"] == "GRAY" ||
+    # metadata["XMP-photoshop:ColorMode"] == "Grayscale" ||
+    # metadata["XMP-photoshop:ICCProfileName"] == "EPSON Gray - Gamma 2.2" ||
+    # metadata["XMP-photoshop:ICCProfileName"] == "Gray Gamma 2.2"
+  end
+
+  # https://exiftool.org/TagNames/EXIF.html
+  def is_rotated?
+    metadata["IFD0:Orientation"].in?(["Rotate 90 CW", "Rotate 270 CW", "Rotate 180"]) ||
+    metadata["IFD1:Orientation"].in?(["Rotate 90 CW", "Rotate 270 CW", "Rotate 180"])
+  end
+
+  # Some animations technically have a finite loop count, but loop for hundreds
+  # or thousands of times. Only count animations with a low loop count as non-repeating.
+  def is_non_repeating_animation?
+    loop_count.in?(0..10)
+  end
+
+  # @see https://exiftool.org/TagNames/GIF.html
+  # @see https://exiftool.org/TagNames/PNG.html
+  # @see https://danbooru.donmai.us/posts?tags=-exif:GIF:AnimationIterations=Infinite+animated_gif
+  # @see https://danbooru.donmai.us/posts?tags=-exif:PNG:AnimationPlays=inf+animated_png
+  def loop_count
+    return Float::INFINITY if metadata["GIF:AnimationIterations"] == "Infinite"
+    return Float::INFINITY if metadata["PNG:AnimationPlays"] == "inf"
+    return metadata["GIF:AnimationIterations"] if metadata["GIF:AnimationIterations"].present?
+    return metadata["PNG:AnimationPlays"] if metadata["PNG:AnimationPlays"].present?
+
+    # If the AnimationIterations tag isn't present, then it's counted as a loop count of 0.
+    return 0 if is_animated_gif? && metadata["GIF:AnimationIterations"].nil?
+
+    nil
+  end
+end
diff --git a/app/models/post.rb b/app/models/post.rb
index ff124de70..4b70f75fb 100644
--- a/app/models/post.rb
+++ b/app/models/post.rb
@@ -498,7 +498,7 @@ class Post < ApplicationRecord
     end
 
     def add_automatic_tags(tags)
-      tags -= %w[incredibly_absurdres absurdres highres lowres huge_filesize flash video ugoira animated_gif animated_png]
+      tags -= %w[incredibly_absurdres absurdres highres lowres huge_filesize flash video ugoira animated_gif animated_png exif_rotation non-repeating_animation]
 
       if image_width >= 10_000 || image_height >= 10_000
         tags << "incredibly_absurdres"
@@ -543,6 +543,10 @@ class Post < ApplicationRecord
       tags << "animated_gif" if media_asset.is_animated_gif?
       tags << "animated_png" if media_asset.is_animated_png?
 
+      tags << "greyscale" if media_asset.is_greyscale?
+      tags << "exif_rotation" if media_asset.is_rotated?
+      tags << "non-repeating_animation" if media_asset.is_non_repeating_animation?
+
       tags
     end
 
diff --git a/test/files/test-animated-86x52-loop-1.gif b/test/files/test-animated-86x52-loop-1.gif
new file mode 100644
index 000000000..966d3a6af
Binary files /dev/null and b/test/files/test-animated-86x52-loop-1.gif differ
diff --git a/test/files/test-animated-86x52-loop-2.gif b/test/files/test-animated-86x52-loop-2.gif
new file mode 100644
index 000000000..6a79df302
Binary files /dev/null and b/test/files/test-animated-86x52-loop-2.gif differ
diff --git a/test/files/test-rotation-90cw.jpg b/test/files/test-rotation-90cw.jpg
new file mode 100644
index 000000000..fc2b837c4
Binary files /dev/null and b/test/files/test-rotation-90cw.jpg differ
diff --git a/test/unit/post_test.rb b/test/unit/post_test.rb
index b9548cf3c..44502e4f2 100644
--- a/test/unit/post_test.rb
+++ b/test/unit/post_test.rb
@@ -1318,6 +1318,38 @@ class PostTest < ActiveSupport::TestCase
         end
       end
 
+      context "a greyscale image missing the greyscale tag" do
+        should "automatically add the greyscale tag" do
+          @media_asset = MediaAsset.create!(file: "test/files/test-grey-no-profile.jpg")
+          @post.update!(md5: @media_asset.md5)
+          @post.reload.update!(tag_string: "tagme")
+          assert_equal("greyscale tagme", @post.tag_string)
+        end
+      end
+
+      context "an exif-rotated image missing the exif_rotation tag" do
+        should "automatically add the exif_rotation tag" do
+          @media_asset = MediaAsset.create!(file: "test/files/test-rotation-90cw.jpg")
+          @post.update!(md5: @media_asset.md5)
+          @post.reload.update!(tag_string: "tagme")
+          assert_equal("exif_rotation tagme", @post.tag_string)
+        end
+      end
+
+      context "a non-repeating GIF missing the non-repeating_animation tag" do
+        should "automatically add the non-repeating_animation tag" do
+          @media_asset = MediaAsset.create!(file: "test/files/test-animated-86x52-loop-1.gif")
+          @post.update!(md5: @media_asset.md5)
+          @post.reload.update!(tag_string: "tagme")
+          assert_equal("animated animated_gif non-repeating_animation tagme", @post.tag_string)
+
+          @media_asset = MediaAsset.create!(file: "test/files/test-animated-86x52-loop-2.gif")
+          @post.update!(md5: @media_asset.md5)
+          @post.reload.update!(tag_string: "tagme")
+          assert_equal("animated animated_gif non-repeating_animation tagme", @post.tag_string)
+        end
+      end
+
       should "have an array representation of its tags" do
         post = FactoryBot.create(:post)
         post.reload