diff --git a/lib/completions/upload_encoder.rb b/lib/completions/upload_encoder.rb
index bd253c96..c2aecbaa 100644
--- a/lib/completions/upload_encoder.rb
+++ b/lib/completions/upload_encoder.rb
@@ -10,6 +10,14 @@ module DiscourseAi
           next if upload.blank?
           next if upload.width.to_i == 0 || upload.height.to_i == 0
 
+          desired_extension = upload.extension
+          desired_extension = "png" if upload.extension == "gif"
+          desired_extension = "png" if upload.extension == "webp"
+          desired_extension = "jpeg" if upload.extension == "jpg"
+
+          # this keeps it very simple format wise given everyone supports png and jpg
+          next if !%w[jpeg png].include?(desired_extension)
+
           original_pixels = upload.width * upload.height
 
           image = upload
@@ -20,12 +28,15 @@ module DiscourseAi
             new_width = (ratio * upload.width).to_i
             new_height = (ratio * upload.height).to_i
 
-            image = upload.get_optimized_image(new_width, new_height)
+            image = upload.get_optimized_image(new_width, new_height, format: desired_extension)
+          elsif upload.extension != desired_extension
+            image =
+              upload.get_optimized_image(upload.width, upload.height, format: desired_extension)
           end
 
           next if !image
 
-          mime_type = MiniMime.lookup_by_filename(upload.original_filename).content_type
+          mime_type = MiniMime.lookup_by_filename("test.#{desired_extension}").content_type
 
           path = Discourse.store.path_for(image)
           if path.blank?
diff --git a/spec/fixtures/images/1x1.gif b/spec/fixtures/images/1x1.gif
new file mode 100644
index 00000000..95a5eff6
Binary files /dev/null and b/spec/fixtures/images/1x1.gif differ
diff --git a/spec/fixtures/images/1x1.jpg b/spec/fixtures/images/1x1.jpg
new file mode 100644
index 00000000..f083de6b
Binary files /dev/null and b/spec/fixtures/images/1x1.jpg differ
diff --git a/spec/fixtures/images/1x1.webp b/spec/fixtures/images/1x1.webp
new file mode 100644
index 00000000..c78718cd
Binary files /dev/null and b/spec/fixtures/images/1x1.webp differ
diff --git a/spec/lib/completions/upload_encoder_spec.rb b/spec/lib/completions/upload_encoder_spec.rb
new file mode 100644
index 00000000..d0434630
--- /dev/null
+++ b/spec/lib/completions/upload_encoder_spec.rb
@@ -0,0 +1,31 @@
+# frozen_string_literal: true
+
+RSpec.describe DiscourseAi::Completions::UploadEncoder do
+  let(:gif) { plugin_file_from_fixtures("1x1.gif") }
+  let(:jpg) { plugin_file_from_fixtures("1x1.jpg") }
+  let(:webp) { plugin_file_from_fixtures("1x1.webp") }
+
+  it "automatically converts gifs to pngs" do
+    upload = UploadCreator.new(gif, "1x1.gif").create_for(Discourse.system_user.id)
+    encoded = described_class.encode(upload_ids: [upload.id], max_pixels: 1_048_576)
+    expect(encoded.length).to eq(1)
+    expect(encoded[0][:base64]).to be_present
+    expect(encoded[0][:mime_type]).to eq("image/png")
+  end
+
+  it "automatically converts webp to pngs" do
+    upload = UploadCreator.new(webp, "1x1.webp").create_for(Discourse.system_user.id)
+    encoded = described_class.encode(upload_ids: [upload.id], max_pixels: 1_048_576)
+    expect(encoded.length).to eq(1)
+    expect(encoded[0][:base64]).to be_present
+    expect(encoded[0][:mime_type]).to eq("image/png")
+  end
+
+  it "supports jpg" do
+    upload = UploadCreator.new(jpg, "1x1.jpg").create_for(Discourse.system_user.id)
+    encoded = described_class.encode(upload_ids: [upload.id], max_pixels: 1_048_576)
+    expect(encoded.length).to eq(1)
+    expect(encoded[0][:base64]).to be_present
+    expect(encoded[0][:mime_type]).to eq("image/jpeg")
+  end
+end