diff --git a/core/src/main/scala/org/http4s/Message.scala b/core/src/main/scala/org/http4s/Message.scala
index ed6c74f7ea4..b00b38ef54f 100644
--- a/core/src/main/scala/org/http4s/Message.scala
+++ b/core/src/main/scala/org/http4s/Message.scala
@@ -294,13 +294,15 @@ sealed abstract case class Request[F[_]](
       attributes = attributes
     )
 
-  lazy val (scriptName, pathInfo) = {
-    val caret = attributes.lookup(Request.Keys.PathInfoCaret).getOrElse(0)
+  lazy val (scriptName, pathInfo) =
     uri.path.splitAt(caret)
-  }
+
+  private def caret =
+    attributes.lookup(Request.Keys.PathInfoCaret).getOrElse(0)
 
   def withPathInfo(pi: String): Self =
-    withUri(uri.withPath(scriptName + pi))
+    // Don't use withUri, which clears the caret
+    copy(uri = uri.withPath(scriptName + pi))
 
   def pathTranslated: Option[File] = attributes.lookup(Keys.PathTranslated)
 
diff --git a/server/src/main/scala/org/http4s/server/middleware/AutoSlash.scala b/server/src/main/scala/org/http4s/server/middleware/AutoSlash.scala
index e131447f6e7..ad76f863ee0 100644
--- a/server/src/main/scala/org/http4s/server/middleware/AutoSlash.scala
+++ b/server/src/main/scala/org/http4s/server/middleware/AutoSlash.scala
@@ -15,22 +15,18 @@ import cats.implicits._
 object AutoSlash {
   def apply[F[_], G[_], B](http: Kleisli[F, Request[G], B])(
       implicit F: MonoidK[F],
-      G: Functor[G]): Kleisli[F, Request[G], B] =
+      G: Functor[G]): Kleisli[F, Request[G], B] = {
+    val _ = G // for binary compatibility in 0.20, remove on master
     Kleisli { req =>
       http(req) <+> {
         val pathInfo = req.pathInfo
-        val scriptName = req.scriptName
 
         if (pathInfo.isEmpty || pathInfo.charAt(pathInfo.length - 1) != '/') {
           F.empty
-        } else if (scriptName.isEmpty) {
-          // Request has not been translated already
-          http.apply(req.withPathInfo(pathInfo.substring(0, pathInfo.length - 1)))
         } else {
-          // Request has been translated at least once, redo the translation
-          val translated = TranslateUri(scriptName)(http)
-          translated.apply(req.withPathInfo(pathInfo.substring(0, pathInfo.length - 1)))
+          http.apply(req.withPathInfo(pathInfo.substring(0, pathInfo.length - 1)))
         }
       }
     }
+  }
 }
diff --git a/tests/src/test/scala/org/http4s/MessageSpec.scala b/tests/src/test/scala/org/http4s/MessageSpec.scala
index f0575896199..859782674df 100644
--- a/tests/src/test/scala/org/http4s/MessageSpec.scala
+++ b/tests/src/test/scala/org/http4s/MessageSpec.scala
@@ -96,6 +96,16 @@ class MessageSpec extends Http4sSpec {
         originalReq.pathInfo mustEqual updatedReq.pathInfo
         originalReq.scriptName mustEqual updatedReq.scriptName
       }
+
+      "preserve caret in withPathInfo" in {
+        val originalReq = Request(
+          uri = Uri(path = "/foo/bar"),
+          attributes = Vault.empty.insert(Request.Keys.PathInfoCaret, 4))
+        val updatedReq = originalReq.withPathInfo("/quux")
+
+        updatedReq.scriptName mustEqual "/foo"
+        updatedReq.pathInfo mustEqual "/quux"
+      }
     }
 
     "toString" should {