diff --git a/lib/route_downcaser/downcase_route_middleware.rb b/lib/route_downcaser/downcase_route_middleware.rb
index 8f50573..f28daa7 100644
--- a/lib/route_downcaser/downcase_route_middleware.rb
+++ b/lib/route_downcaser/downcase_route_middleware.rb
@@ -20,6 +20,7 @@ def _call(env)
 
       # Downcase path_info if applicable
       path_info = downcased_uri(path_info)
+      path_info = path_info.gsub('%7E', '~') if path_info
 
       # If redirect configured, then return redirect request, if either
       # path_info has changed
diff --git a/test/integration/route_middleware_test.rb b/test/integration/route_middleware_test.rb
index 12c1f5a..b6f4c96 100644
--- a/test/integration/route_middleware_test.rb
+++ b/test/integration/route_middleware_test.rb
@@ -58,6 +58,15 @@ def call(env)
     assert_equal "/пиво", URI.decode_www_form_component(response.location)
   end
 
+  test "Can downcase path with tilde correctly" do
+    RouteDowncaser.configuration do |config|
+      config.redirect = true
+    end
+    get "/~Test~~test"
+    assert_equal 301, response.status
+    assert_equal "/~test~~test", URI.decode_www_form_component(response.location)
+  end
+
   test "Can downcase longer unicode paths correctly" do
     RouteDowncaser.configuration do |config|
       config.redirect = true
diff --git a/test/route_downcaser_test.rb b/test/route_downcaser_test.rb
index 6e61cc7..48a6288 100644
--- a/test/route_downcaser_test.rb
+++ b/test/route_downcaser_test.rb
@@ -122,4 +122,27 @@ class MultibyteRedirectTests < ActiveSupport::TestCase
       assert_instance_of String, headers["Location"], "Headers must be strings"
     end
   end
+
+  class SpecialSymbolsInPathTests < ActiveSupport::TestCase
+    setup do
+      @app = MyMockApp.new
+      RouteDowncaser.configuration do |config|
+        config.redirect = true
+        config.exclude_patterns = nil
+      end
+    end
+
+    test "path with tildes" do
+      callenv = {"PATH_INFO" => "/~test~~test~", "REQUEST_METHOD" => "GET"}
+      RouteDowncaser::DowncaseRouteMiddleware.new(@app).call(callenv)
+      assert_equal("/~test~~test~", @app.env["PATH_INFO"])
+    end
+
+    test "path with escape tilde" do
+      callenv = {"PATH_INFO" => "/~test%7Etest~~", "REQUEST_METHOD" => "GET"}
+      status, headers, _ = *RouteDowncaser::DowncaseRouteMiddleware.new(@app).call(callenv)
+      assert_equal 301, status
+      assert_equal("/~test~test~~", headers["Location"])
+    end
+  end
 end