diff --git a/cli/rt/11_url.js b/cli/rt/11_url.js
index a7200f11c4..7e01f4d887 100644
--- a/cli/rt/11_url.js
+++ b/cli/rt/11_url.js
@@ -370,7 +370,7 @@
     }
     if (usedNonBase || restUrl.startsWith("?")) {
       [parts.query, restUrl] = takePattern(restUrl, /^(\?[^#]*)/);
-      parts.query = encodeSearch(parts.query);
+      parts.query = encodeSearch(parts.query, isSpecial);
       usedNonBase = true;
     } else {
       parts.query = baseParts.query;
@@ -660,7 +660,8 @@
     set search(value) {
       value = String(value);
       const query = value == "" || value.charAt(0) == "?" ? value : `?${value}`;
-      parts.get(this).query = encodeSearch(query);
+      const isSpecial = specialSchemes.includes(parts.get(this).protocol);
+      parts.get(this).query = encodeSearch(query, isSpecial);
       this.#updateSearchParams();
     }
 
@@ -766,9 +767,9 @@
     return (c >= "\u0000" && c <= "\u001F") || c > "\u007E";
   }
 
-  function charInSearchSet(c) {
+  function charInSearchSet(c, isSpecial) {
     // deno-fmt-ignore
-    return charInC0ControlSet(c) || ["\u0020", "\u0022", "\u0023", "\u0027", "\u003C", "\u003E"].includes(c) || c > "\u007E";
+    return charInC0ControlSet(c) || ["\u0020", "\u0022", "\u0023", "\u003C", "\u003E"].includes(c) || isSpecial && c == "\u0027" || c > "\u007E";
   }
 
   function charInFragmentSet(c) {
@@ -871,8 +872,10 @@
     return [...s].map((c) => (charInPathSet(c) ? encodeChar(c) : c)).join("");
   }
 
-  function encodeSearch(s) {
-    return [...s].map((c) => (charInSearchSet(c) ? encodeChar(c) : c)).join("");
+  function encodeSearch(s, isSpecial) {
+    return [...s].map((
+      c,
+    ) => (charInSearchSet(c, isSpecial) ? encodeChar(c) : c)).join("");
   }
 
   function encodeHash(s) {
diff --git a/cli/tests/unit/url_test.ts b/cli/tests/unit/url_test.ts
index ed8ae55001..438e80892d 100644
--- a/cli/tests/unit/url_test.ts
+++ b/cli/tests/unit/url_test.ts
@@ -272,26 +272,30 @@ unitTest(function urlTrim() {
 
 unitTest(function urlEncoding() {
   assertEquals(
-    new URL("https://a !$&*()=,;+'\"@example.com").username,
+    new URL("http://a !$&*()=,;+'\"@example.com").username,
     "a%20!$&*()%3D,%3B+%27%22",
   );
   assertEquals(
-    new URL("https://:a !$&*()=,;+'\"@example.com").password,
+    new URL("http://:a !$&*()=,;+'\"@example.com").password,
     "a%20!$&*()%3D,%3B+%27%22",
   );
-  assertEquals(new URL("abcde://mañana/c?d#e").hostname, "ma%C3%B1ana");
   // https://url.spec.whatwg.org/#idna
-  assertEquals(new URL("https://mañana/c?d#e").hostname, "xn--maana-pta");
+  assertEquals(new URL("http://mañana/c?d#e").hostname, "xn--maana-pta");
+  assertEquals(new URL("abcd://mañana/c?d#e").hostname, "ma%C3%B1ana");
   assertEquals(
-    new URL("https://example.com/a ~!@$&*()=:/,;+'\"\\").pathname,
+    new URL("http://example.com/a ~!@$&*()=:/,;+'\"\\").pathname,
     "/a%20~!@$&*()=:/,;+'%22/",
   );
   assertEquals(
-    new URL("https://example.com?a ~!@$&*()=:/,;?+'\"\\").search,
+    new URL("http://example.com?a ~!@$&*()=:/,;?+'\"\\").search,
     "?a%20~!@$&*()=:/,;?+%27%22\\",
   );
   assertEquals(
-    new URL("https://example.com#a ~!@#$&*()=:/,;?+'\"\\").hash,
+    new URL("abcd://example.com?a ~!@$&*()=:/,;?+'\"\\").search,
+    "?a%20~!@$&*()=:/,;?+'%22\\",
+  );
+  assertEquals(
+    new URL("http://example.com#a ~!@#$&*()=:/,;?+'\"\\").hash,
     "#a%20~!@#$&*()=:/,;?+'%22\\",
   );
 });