diff --git a/config/routes.rb b/config/routes.rb
index 615f1f6a88a..8e27a365b08 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -528,7 +528,7 @@ Discourse::Application.routes.draw do
 
     # used to download original images
     get "uploads/:site/:sha(.:extension)" => "uploads#show", constraints: { site: /\w+/, sha: /\h{40}/, extension: /[a-z0-9\._]+/i }
-    get "uploads/short-url/:base62(.:extension)" => "uploads#show_short", constraints: { site: /\w+/, base62: /[a-zA-Z0-9]+/, extension: /[a-z0-9\._]+/i }, as: :upload_short
+    get "uploads/short-url/:base62(.:extension)" => "uploads#show_short", constraints: { site: /\w+/, base62: /[a-zA-Z0-9]+/, extension: /[a-zA-Z0-9\._-]+/i }, as: :upload_short
     # used to download attachments
     get "uploads/:site/original/:tree:sha(.:extension)" => "uploads#show", constraints: { site: /\w+/, tree: /([a-z0-9]+\/)+/i, sha: /\h{40}/, extension: /[a-z0-9\._]+/i }
     if Rails.env.test?
diff --git a/spec/fixtures/images/fake.long-FileExtension b/spec/fixtures/images/fake.long-FileExtension
new file mode 100644
index 00000000000..a6a874af9ee
--- /dev/null
+++ b/spec/fixtures/images/fake.long-FileExtension
@@ -0,0 +1 @@
+https://meta.discourse.org/t/uploading-files-with-longer-file-extensions-gets-truncated/182824
diff --git a/spec/lib/upload_creator_spec.rb b/spec/lib/upload_creator_spec.rb
index fdf08347b4d..67e67dac490 100644
--- a/spec/lib/upload_creator_spec.rb
+++ b/spec/lib/upload_creator_spec.rb
@@ -9,7 +9,7 @@ RSpec.describe UploadCreator do
   describe '#create_for' do
     describe 'when upload is not an image' do
       before do
-        SiteSetting.authorized_extensions = 'txt'
+        SiteSetting.authorized_extensions = 'txt|long-FileExtension'
       end
 
       let(:filename) { "utf-8.txt" }
@@ -38,6 +38,19 @@ RSpec.describe UploadCreator do
         expect(user2.user_uploads.count).to eq(1)
         expect(upload.user_uploads.count).to eq(2)
       end
+
+      let(:longextension) { "fake.long-FileExtension" }
+      let(:file2) { file_from_fixtures(longextension) }
+
+      it 'should truncate long extension names' do
+        expect do
+          UploadCreator.new(file2, "fake.long-FileExtension").create_for(user.id)
+        end.to change { Upload.count }.by(1)
+
+        upload = Upload.last
+
+        expect(upload.extension).to eq('long-FileE')
+      end
     end
 
     describe 'when image is not authorized' do
diff --git a/spec/requests/uploads_controller_spec.rb b/spec/requests/uploads_controller_spec.rb
index 1e7769c1c69..9b7201ad78c 100644
--- a/spec/requests/uploads_controller_spec.rb
+++ b/spec/requests/uploads_controller_spec.rb
@@ -365,6 +365,13 @@ describe UploadsController do
         expect(response.status).to eq(200)
       end
 
+      it "returns uploads with a dash and uppercase in extension correctly" do
+        fake_upload = upload_file("fake.long-FileExtension")
+        get fake_upload.short_path
+
+        expect(response.status).to eq(200)
+      end
+
       it "returns the right response when anon tries to download a file " \
         "when prevent_anons_from_downloading_files is true" do