diff --git a/spec/std/http/server/handlers/static_file_handler_spec.cr b/spec/std/http/server/handlers/static_file_handler_spec.cr
index f4de1cf6ba58..d63629ba5236 100644
--- a/spec/std/http/server/handlers/static_file_handler_spec.cr
+++ b/spec/std/http/server/handlers/static_file_handler_spec.cr
@@ -124,4 +124,13 @@ describe HTTP::StaticFileHandler do
       response.status_code.should eq(400)
     end
   end
+
+  it "handles invalid redirect path" do
+    response = handle HTTP::Request.new("GET", "test.txt%0A")
+    response.status_code.should eq(302)
+    response.headers["Location"].should eq "/test.txt%0A"
+
+    response = handle HTTP::Request.new("GET", "/test.txt%0A")
+    response.status_code.should eq(404)
+  end
 end
diff --git a/src/http/server/handlers/static_file_handler.cr b/src/http/server/handlers/static_file_handler.cr
index fdc17bcfc54d..7aa49fb1ac5b 100644
--- a/src/http/server/handlers/static_file_handler.cr
+++ b/src/http/server/handlers/static_file_handler.cr
@@ -99,7 +99,7 @@ class HTTP::StaticFileHandler
   private def redirect_to(context, url)
     context.response.status_code = 302
 
-    url = URI.escape(url) { |b| URI.unreserved?(b) || b != '/' }
+    url = URI.escape(url) { |byte| URI.unreserved?(byte) || byte.chr == '/' }
     context.response.headers.add "Location", url
   end