diff --git a/caddyhttp/rewrite/rewrite.go b/caddyhttp/rewrite/rewrite.go
index f7f56cd39..634b7555c 100644
--- a/caddyhttp/rewrite/rewrite.go
+++ b/caddyhttp/rewrite/rewrite.go
@@ -95,9 +95,15 @@ func (s *SimpleRule) Match(r *http.Request) bool {
 
 // Rewrite rewrites the internal location of the current request.
 func (s *SimpleRule) Rewrite(fs http.FileSystem, r *http.Request) Result {
+	matches := regexpMatches(s.Regexp, "/", r.URL.Path)
+
+	replacer := newReplacer(r)
+	for i := 1; i < len(matches); i++ {
+		replacer.Set(fmt.Sprint(i), matches[i])
+	}
 
 	// attempt rewrite
-	return To(fs, r, s.To, newReplacer(r))
+	return To(fs, r, s.To, replacer)
 }
 
 // ComplexRule is a rewrite rule based on a regular expression
@@ -198,16 +204,7 @@ func (r ComplexRule) Rewrite(fs http.FileSystem, req *http.Request) (re Result)
 		default:
 			// set regexp match variables {1}, {2} ...
 
-			// url escaped values of ? and #.
-			q, f := url.QueryEscape("?"), url.QueryEscape("#")
-
 			for i := 1; i < len(matches); i++ {
-				// Special case of unescaped # and ? by stdlib regexp.
-				// Reverse the unescape.
-				if strings.ContainsAny(matches[i], "?#") {
-					matches[i] = strings.NewReplacer("?", q, "#", f).Replace(matches[i])
-				}
-
 				replacer.Set(fmt.Sprint(i), matches[i])
 			}
 		}
@@ -246,6 +243,8 @@ func (r ComplexRule) matchExt(rPath string) bool {
 	return !mustUse
 }
 
+var escaper = strings.NewReplacer("?", url.QueryEscape("?"), "#", url.QueryEscape("#"))
+
 func regexpMatches(regexp *regexp.Regexp, base, rPath string) []string {
 	if regexp != nil {
 		// include trailing slash in regexp if present
@@ -253,7 +252,19 @@ func regexpMatches(regexp *regexp.Regexp, base, rPath string) []string {
 		if strings.HasSuffix(base, "/") {
 			start--
 		}
-		return regexp.FindStringSubmatch(rPath[start:])
+
+		matches := regexp.FindStringSubmatch(rPath[start:])
+
+		// When processing a rewrite rule, the matching is done with an unescaped
+		// version of the old path. However, when such a match contains a ? or #
+		// character, the match cannot be used verbatim in the "to" URL because
+		// there it would be interpreted as query/fragment marker, so we re-escape
+		// those characters:
+		for i := 1; i < len(matches); i++ {
+			matches[i] = escaper.Replace(matches[i])
+		}
+
+		return matches
 	}
 	return nil
 }
diff --git a/caddyhttp/rewrite/rewrite_test.go b/caddyhttp/rewrite/rewrite_test.go
index 82cea5a23..b20d91eff 100644
--- a/caddyhttp/rewrite/rewrite_test.go
+++ b/caddyhttp/rewrite/rewrite_test.go
@@ -33,6 +33,7 @@ func TestRewrite(t *testing.T) {
 			newSimpleRule(t, "^/from$", "/to"),
 			newSimpleRule(t, "^/a$", "/b"),
 			newSimpleRule(t, "^/b$", "/b{uri}"),
+			newSimpleRule(t, "^/simplereggrp/([0-9]+)([a-z]*)$", "/{1}/{2}/{query}"),
 		},
 		FileSys: http.Dir("."),
 	}
@@ -113,6 +114,7 @@ func TestRewrite(t *testing.T) {
 		{"/hashtest/a%20%23%20test", "/a%20%23%20test"},
 		{"/hashtest/a%20%3F%20test", "/a%20%3F%20test"},
 		{"/hashtest/a%20%3F%23test", "/a%20%3F%23test"},
+		{"/simplereggrp/123abc?q", "/123/abc/q?q"},
 	}
 
 	for i, test := range tests {
@@ -129,7 +131,7 @@ func TestRewrite(t *testing.T) {
 		}
 
 		if got, want := rec.Body.String(), test.expectedTo; got != want {
-			t.Errorf("Test %d: Expected URL to be '%s' but was '%s'", i, want, got)
+			t.Errorf("Test %d: Expected URL '%s' to be rewritten to '%s' but was rewritten to '%s'", i, test.from, want, got)
 		}
 	}
 }