diff --git a/okhttp/src/commonJvmAndroid/kotlin/okhttp3/HttpUrl.kt b/okhttp/src/commonJvmAndroid/kotlin/okhttp3/HttpUrl.kt
index 646c698437e2..6343bf707656 100644
--- a/okhttp/src/commonJvmAndroid/kotlin/okhttp3/HttpUrl.kt
+++ b/okhttp/src/commonJvmAndroid/kotlin/okhttp3/HttpUrl.kt
@@ -32,6 +32,7 @@ import okhttp3.internal.url.FRAGMENT_ENCODE_SET
 import okhttp3.internal.url.FRAGMENT_ENCODE_SET_URI
 import okhttp3.internal.url.PASSWORD_ENCODE_SET
 import okhttp3.internal.url.PATH_SEGMENT_ENCODE_SET
+import okhttp3.internal.url.PATH_SEGMENT_ENCODE_SET_RAW
 import okhttp3.internal.url.PATH_SEGMENT_ENCODE_SET_URI
 import okhttp3.internal.url.QUERY_COMPONENT_ENCODE_SET
 import okhttp3.internal.url.QUERY_COMPONENT_ENCODE_SET_URI
@@ -1045,7 +1046,7 @@ class HttpUrl private constructor(
       index: Int,
       pathSegment: String,
     ) = apply {
-      val canonicalPathSegment = pathSegment.canonicalize(encodeSet = PATH_SEGMENT_ENCODE_SET)
+      val canonicalPathSegment = pathSegment.canonicalize(encodeSet = PATH_SEGMENT_ENCODE_SET_RAW)
       require(!isDot(canonicalPathSegment) && !isDotDot(canonicalPathSegment)) {
         "unexpected path segment: $pathSegment"
       }
@@ -1547,7 +1548,7 @@ class HttpUrl private constructor(
         input.canonicalize(
           pos = pos,
           limit = limit,
-          encodeSet = PATH_SEGMENT_ENCODE_SET,
+          encodeSet = if (alreadyEncoded) PATH_SEGMENT_ENCODE_SET else PATH_SEGMENT_ENCODE_SET_RAW,
           alreadyEncoded = alreadyEncoded,
         )
       if (isDot(segment)) {
diff --git a/okhttp/src/commonJvmAndroid/kotlin/okhttp3/internal/url/-Url.kt b/okhttp/src/commonJvmAndroid/kotlin/okhttp3/internal/url/-Url.kt
index f3380485e1a0..50fb00550617 100644
--- a/okhttp/src/commonJvmAndroid/kotlin/okhttp3/internal/url/-Url.kt
+++ b/okhttp/src/commonJvmAndroid/kotlin/okhttp3/internal/url/-Url.kt
@@ -26,6 +26,7 @@ internal val HEX_DIGITS =
 internal const val USERNAME_ENCODE_SET = " \"':;<=>@[]^`{}|/\\?#"
 internal const val PASSWORD_ENCODE_SET = " \"':;<=>@[]^`{}|/\\?#"
 internal const val PATH_SEGMENT_ENCODE_SET = " \"<>^`{}|/\\?#"
+internal const val PATH_SEGMENT_ENCODE_SET_RAW = " \"<>^`{}|/\\?#[]"
 internal const val PATH_SEGMENT_ENCODE_SET_URI = "[]"
 internal const val QUERY_ENCODE_SET = " \"'<>#"
 internal const val QUERY_COMPONENT_REENCODE_SET = " \"'<>#&="
diff --git a/okhttp/src/jvmTest/kotlin/okhttp3/HttpUrlJvmTest.kt b/okhttp/src/jvmTest/kotlin/okhttp3/HttpUrlJvmTest.kt
index 217c6c14c48b..01c40bbe1eb9 100644
--- a/okhttp/src/jvmTest/kotlin/okhttp3/HttpUrlJvmTest.kt
+++ b/okhttp/src/jvmTest/kotlin/okhttp3/HttpUrlJvmTest.kt
@@ -263,7 +263,7 @@ open class HttpUrlJvmTest {
         .addPathSegment("=[]:;\"~|?#@^/$%*")
         .build()
     assertThat(url.toString())
-      .isEqualTo("http://host/=[]:;%22~%7C%3F%23@%5E%2F$%25*")
+      .isEqualTo("http://host/=%5B%5D:;%22~%7C%3F%23@%5E%2F$%25*")
     assertThat(url.toUri().toString())
       .isEqualTo("http://host/=%5B%5D:;%22~%7C%3F%23@%5E%2F$%25*")
   }
diff --git a/okhttp/src/jvmTest/kotlin/okhttp3/HttpUrlTest.kt b/okhttp/src/jvmTest/kotlin/okhttp3/HttpUrlTest.kt
index 9ada0b3ee425..fce91f447e66 100644
--- a/okhttp/src/jvmTest/kotlin/okhttp3/HttpUrlTest.kt
+++ b/okhttp/src/jvmTest/kotlin/okhttp3/HttpUrlTest.kt
@@ -1535,6 +1535,35 @@ open class HttpUrlTest {
     ).isEqualTo("/a/b/c/%252e%252e")
   }
 
+  @Test
+  fun addPathSegmentEncodesSquareBrackets() {
+    val url =
+      parse("http://host/")
+        .newBuilder()
+        .addPathSegment("a[0]")
+        .build()
+    assertThat(url.encodedPath).isEqualTo("/a%5B0%5D")
+    assertThat(url.pathSegments).containsExactly("a[0]")
+  }
+
+  @Test
+  fun addEncodedPathSegmentRetainsSquareBrackets() {
+    val url =
+      parse("http://host/")
+        .newBuilder()
+        .addEncodedPathSegment("a[0]")
+        .build()
+    assertThat(url.encodedPath).isEqualTo("/a[0]")
+    assertThat(url.pathSegments).containsExactly("a[0]")
+  }
+
+  @Test
+  fun parseRetainsSquareBracketsInPath() {
+    val url = parse("http://host/a[0]")
+    assertThat(url.encodedPath).isEqualTo("/a[0]")
+    assertThat(url.pathSegments).containsExactly("a[0]")
+  }
+
   @Test
   fun addPathSegmentDotDotPopsDirectory() {
     val base = parse("http://host/a/b/c")
@@ -1635,6 +1664,17 @@ open class HttpUrlTest {
     ).isEqualTo("/%252e/b/c")
   }
 
+  @Test
+  fun setPathSegmentEncodesSquareBrackets() {
+    val url =
+      parse("http://host/a/b/c")
+        .newBuilder()
+        .setPathSegment(0, "x[0]")
+        .build()
+    assertThat(url.encodedPath).isEqualTo("/x%5B0%5D/b/c")
+    assertThat(url.pathSegments).containsExactly("x[0]", "b", "c")
+  }
+
   @Test
   fun setPathSegmentAcceptsEmpty() {
     val base = parse("http://host/a/b/c")