diff --git a/build.sbt b/build.sbt
index dc27ae46d4..5254ea26ee 100644
--- a/build.sbt
+++ b/build.sbt
@@ -209,7 +209,7 @@ lazy val zioHttpBenchmarks = (project in file("zio-http-benchmarks"))
 //      "com.softwaremill.sttp.tapir" %% "tapir-akka-http-server" % "1.1.0",
       "com.softwaremill.sttp.tapir"   %% "tapir-http4s-server" % "1.5.1",
       "com.softwaremill.sttp.tapir"   %% "tapir-json-circe"    % "1.5.1",
-      "com.softwaremill.sttp.client3" %% "core"                % "3.9.0",
+      "com.softwaremill.sttp.client3" %% "core"                % "3.9.1",
 //      "dev.zio"                     %% "zio-interop-cats"    % "3.3.0",
       "org.slf4j"                      % "slf4j-api"           % "2.0.9",
       "org.slf4j"                      % "slf4j-simple"        % "2.0.9",
diff --git a/project/Dependencies.scala b/project/Dependencies.scala
index 3d116e277d..2021be2583 100644
--- a/project/Dependencies.scala
+++ b/project/Dependencies.scala
@@ -3,10 +3,10 @@ import sbt.Keys.scalaVersion
 
 object Dependencies {
   val JwtCoreVersion                = "9.1.1"
-  val NettyVersion                  = "4.1.100.Final"
+  val NettyVersion                  = "4.1.101.Final"
   val NettyIncubatorVersion         = "0.0.20.Final"
   val ScalaCompactCollectionVersion = "2.11.0"
-  val ZioVersion                    = "2.0.18"
+  val ZioVersion                    = "2.0.19"
   val ZioCliVersion                 = "0.5.0"
   val ZioSchemaVersion              = "0.4.15"
   val SttpVersion                   = "3.3.18"
diff --git a/project/build.properties b/project/build.properties
index 27430827bc..e8a1e246e8 100644
--- a/project/build.properties
+++ b/project/build.properties
@@ -1 +1 @@
-sbt.version=1.9.6
+sbt.version=1.9.7
diff --git a/project/plugins.sbt b/project/plugins.sbt
index 989c03b398..540cfc7eff 100644
--- a/project/plugins.sbt
+++ b/project/plugins.sbt
@@ -3,7 +3,7 @@ addSbtPlugin("org.scalameta"      % "sbt-scalafmt"       % "2.5.0")
 addSbtPlugin("pl.project13.scala" % "sbt-jmh"            % "0.4.6")
 addSbtPlugin("com.timushev.sbt"   % "sbt-updates"        % "0.6.3")
 addSbtPlugin("io.spray"           % "sbt-revolver"       % "0.10.0")
-addSbtPlugin("com.github.sbt"     % "sbt-github-actions" % "0.18.0")
+addSbtPlugin("com.github.sbt"     % "sbt-github-actions" % "0.19.0")
 addSbtPlugin("com.github.sbt"     % "sbt-ci-release"     % "1.5.12")
 addSbtPlugin("dev.zio"            % "zio-sbt-website"    % "0.3.10")
 addSbtPlugin("de.heikoseeberger"  % "sbt-header"         % "5.10.0")
diff --git a/zio-http/src/main/scala/zio/http/Handler.scala b/zio-http/src/main/scala/zio/http/Handler.scala
index 52bb0ea89a..851a8be2af 100644
--- a/zio-http/src/main/scala/zio/http/Handler.scala
+++ b/zio-http/src/main/scala/zio/http/Handler.scala
@@ -367,6 +367,19 @@ sealed trait Handler[-R, +Err, -In, +Out] { self =>
   ): Handler[R1, Err1, In, Out1] =
     self.foldHandler(err => Handler.fromZIO(f(err)), Handler.succeed(_))
 
+  /**
+   * Transforms all failures of the handler effectfully except pure
+   * interruption.
+   */
+  final def mapErrorCauseZIO[R1 <: R, Err1, Out1 >: Out](
+    f: Cause[Err] => ZIO[R1, Err1, Out1],
+  )(implicit trace: Trace): Handler[R1, Err1, In, Out1] =
+    self.foldCauseHandler(
+      err =>
+        if (err.isInterruptedOnly) Handler.failCause(err.asInstanceOf[Cause[Nothing]]) else Handler.fromZIO(f(err)),
+      Handler.succeed(_),
+    )
+
   /**
    * Returns a new handler where the error channel has been merged into the
    * success channel to their common combined type.
diff --git a/zio-http/src/main/scala/zio/http/Middleware.scala b/zio-http/src/main/scala/zio/http/Middleware.scala
index 5f5a9212e7..1324f9a81c 100644
--- a/zio-http/src/main/scala/zio/http/Middleware.scala
+++ b/zio-http/src/main/scala/zio/http/Middleware.scala
@@ -170,6 +170,68 @@ object Middleware extends HandlerAspects {
     }
   }
 
+  def logAnnotate(key: => String, value: => String)(implicit trace: Trace): Middleware[Any] =
+    logAnnotate(LogAnnotation(key, value))
+
+  def logAnnotate(logAnnotation: => LogAnnotation, logAnnotations: LogAnnotation*)(implicit
+    trace: Trace,
+  ): Middleware[Any] =
+    logAnnotate((logAnnotation +: logAnnotations).toSet)
+
+  def logAnnotate(logAnnotations: => Set[LogAnnotation])(implicit trace: Trace): Middleware[Any] =
+    new Middleware[Any] {
+      def apply[Env1 <: Any, Err](routes: Routes[Env1, Err]): Routes[Env1, Err] =
+        routes.transform[Env1] { h =>
+          handler((req: Request) => ZIO.logAnnotate(logAnnotations)(h(req)))
+        }
+    }
+
+  /**
+   * Creates a middleware that will annotate log messages that are logged while
+   * a request is handled with log annotations derived from the request.
+   */
+  def logAnnotate(fromRequest: Request => Set[LogAnnotation])(implicit trace: Trace): Middleware[Any] =
+    new Middleware[Any] {
+      def apply[Env1 <: Any, Err](routes: Routes[Env1, Err]): Routes[Env1, Err] =
+        routes.transform[Env1] { h =>
+          handler((req: Request) => ZIO.logAnnotate(fromRequest(req))(h(req)))
+        }
+    }
+
+  /**
+   * Creates a middleware that will annotate log messages that are logged while
+   * a request is handled with the names and the values of the specified
+   * headers.
+   */
+  def logAnnotateHeaders(headerName: String, headerNames: String*)(implicit trace: Trace): Middleware[Any] =
+    new Middleware[Any] {
+      def apply[Env1 <: Any, Err](routes: Routes[Env1, Err]): Routes[Env1, Err] = {
+        val headers = headerName +: headerNames
+        routes.transform[Env1] { h =>
+          handler((req: Request) => {
+            val annotations = Set.newBuilder[LogAnnotation]
+            annotations.sizeHint(headers.length)
+            var i           = 0
+            while (i < headers.length) {
+              val name = headers(i)
+              annotations += LogAnnotation(name, req.headers.get(name).mkString)
+              i += 1
+            }
+            ZIO.logAnnotate(annotations.result())(h(req))
+          })
+        }
+      }
+    }
+
+  /**
+   * Creates middleware that will annotate log messages that are logged while a
+   * request is handled with the names and the values of the specified headers.
+   */
+  def logAnnotateHeaders(header: Header.HeaderType, headers: Header.HeaderType*)(implicit
+    trace: Trace,
+  ): Middleware[Any] =
+    logAnnotateHeaders(header.name, headers.map(_.name): _*)
+
   def timeout(duration: Duration)(implicit trace: Trace): Middleware[Any] =
     new Middleware[Any] {
       def apply[Env1 <: Any, Err](routes: Routes[Env1, Err]): Routes[Env1, Err] =
@@ -284,7 +346,8 @@ object Middleware extends HandlerAspects {
       }
 
       override def apply[Env1 <: Any, Err](routes: Routes[Env1, Err]): Routes[Env1, Err] = {
-        val mountpoint = Method.GET / path.segments.map(PathCodec.literal).reduceLeft(_ / _)
+        val mountpoint =
+          Method.GET / path.segments.map(PathCodec.literal).reduceLeftOption(_ / _).getOrElse(PathCodec.empty)
         val pattern    = mountpoint / trailing
         val other      = Routes(
           pattern -> Handler
diff --git a/zio-http/src/main/scala/zio/http/Route.scala b/zio-http/src/main/scala/zio/http/Route.scala
index 0e0ec8334e..c51d6fc207 100644
--- a/zio-http/src/main/scala/zio/http/Route.scala
+++ b/zio-http/src/main/scala/zio/http/Route.scala
@@ -83,6 +83,32 @@ sealed trait Route[-Env, +Err] { self =>
         Handled(rpm.routePattern, handler2, location)
     }
 
+  final def handleErrorCauseZIO(
+    f: Cause[Err] => ZIO[Any, Nothing, Response],
+  )(implicit trace: Trace): Route[Env, Nothing] =
+    self match {
+      case Provided(route, env)                     => Provided(route.handleErrorCauseZIO(f), env)
+      case Augmented(route, aspect)                 => Augmented(route.handleErrorCauseZIO(f), aspect)
+      case Handled(routePattern, handler, location) => Handled(routePattern, handler, location)
+
+      case Unhandled(rpm, handler, zippable, location) =>
+        val handler2: Handler[Env, Response, Request, Response] = {
+          val paramHandler =
+            Handler.fromFunctionZIO[(rpm.Context, Request)] { case (ctx, request) =>
+              rpm.routePattern.decode(request.method, request.path) match {
+                case Left(error)  => ZIO.dieMessage(error)
+                case Right(value) =>
+                  val params = rpm.zippable.zip(value, ctx)
+
+                  handler(zippable.zip(params, request))
+              }
+            }
+          rpm.aspect.applyHandlerContext(paramHandler.mapErrorCauseZIO(f))
+        }
+
+        Handled(rpm.routePattern, handler2, location)
+    }
+
   /**
    * Determines if the route is defined for the specified request.
    */
diff --git a/zio-http/src/main/scala/zio/http/RoutePattern.scala b/zio-http/src/main/scala/zio/http/RoutePattern.scala
index 2dc33c00f9..932605e0bf 100644
--- a/zio-http/src/main/scala/zio/http/RoutePattern.scala
+++ b/zio-http/src/main/scala/zio/http/RoutePattern.scala
@@ -222,16 +222,16 @@ object RoutePattern {
    */
   val any: RoutePattern[Path] = RoutePattern(Method.ANY, PathCodec.trailing)
 
+  def apply(method: Method, path: Path): RoutePattern[Unit] =
+    path.segments.foldLeft[RoutePattern[Unit]](fromMethod(method)) { (pathSpec, segment) =>
+      pathSpec./[Unit](PathCodec.Segment(SegmentCodec.literal(segment)))
+    }
+
   /**
    * Constructs a route pattern from a method and a path literal. To match
    * against any method, use [[zio.http.Method.ANY]]. The specified string may
    * contain path segments, which are separated by slashes.
    */
-  def apply(method: Method, value: String): RoutePattern[Unit] = {
-    val path = Path(value)
-
-    path.segments.foldLeft[RoutePattern[Unit]](fromMethod(method)) { (pathSpec, segment) =>
-      pathSpec./[Unit](PathCodec.Segment(SegmentCodec.literal(segment)))
-    }
-  }
+  def apply(method: Method, pathString: String): RoutePattern[Unit] =
+    apply(method, Path(pathString))
 }
diff --git a/zio-http/src/main/scala/zio/http/Routes.scala b/zio-http/src/main/scala/zio/http/Routes.scala
index bc8845d1d1..3fb19c5781 100644
--- a/zio-http/src/main/scala/zio/http/Routes.scala
+++ b/zio-http/src/main/scala/zio/http/Routes.scala
@@ -76,6 +76,9 @@ final class Routes[-Env, +Err] private (val routes: Chunk[zio.http.Route[Env, Er
   def handleErrorCause(f: Cause[Err] => Response)(implicit trace: Trace): Routes[Env, Nothing] =
     new Routes(routes.map(_.handleErrorCause(f)))
 
+  def handleErrorCauseZIO(f: Cause[Err] => ZIO[Any, Nothing, Response])(implicit trace: Trace): Routes[Env, Nothing] =
+    new Routes(routes.map(_.handleErrorCauseZIO(f)))
+
   /**
    * Returns new routes that have each been provided the specified environment,
    * thus eliminating their requirement for any specific environment.
diff --git a/zio-http/src/test/scala/zio/http/LogAnnotationMiddlewareSpec.scala b/zio-http/src/test/scala/zio/http/LogAnnotationMiddlewareSpec.scala
new file mode 100644
index 0000000000..f9f58b5a1f
--- /dev/null
+++ b/zio-http/src/test/scala/zio/http/LogAnnotationMiddlewareSpec.scala
@@ -0,0 +1,72 @@
+package zio.http
+
+import zio._
+import zio.test._
+
+object LogAnnotationMiddlewareSpec extends ZIOSpecDefault {
+  override def spec: Spec[TestEnvironment with Scope, Any] =
+    suite("LogAnnotationMiddlewareSpec")(
+      test("add static log annotation") {
+        val response = Routes
+          .singleton(
+            handler(ZIO.logWarning("Oh!") *> ZIO.succeed(Response.text("Hey logging!"))),
+          )
+          .@@(Middleware.logAnnotate("label", "value"))
+          .toHttpApp
+          .runZIO(Request.get("/"))
+
+        for {
+          _    <- response
+          logs <- ZTestLogger.logOutput
+          log = logs.filter(_.message() == "Oh!").head
+        } yield assertTrue(log.annotations.get("label").contains("value"))
+
+      },
+      test("add request method and path as annotation") {
+        val response = Routes
+          .singleton(
+            handler(ZIO.logWarning("Oh!") *> ZIO.succeed(Response.text("Hey logging!"))),
+          )
+          .@@(
+            Middleware.logAnnotate(req =>
+              Set(LogAnnotation("method", req.method.name), LogAnnotation("path", req.path.encode)),
+            ),
+          )
+          .toHttpApp
+          .runZIO(Request.get("/"))
+
+        for {
+          _    <- response
+          logs <- ZTestLogger.logOutput
+          log = logs.filter(_.message() == "Oh!").head
+        } yield assertTrue(
+          log.annotations.get("method").contains("GET"),
+          log.annotations.get("path").contains("/"),
+        )
+      },
+      test("add headers as annotation") {
+        val response = Routes
+          .singleton(
+            handler(ZIO.logWarning("Oh!") *> ZIO.succeed(Response.text("Hey logging!"))),
+          )
+          .@@(Middleware.logAnnotateHeaders("header"))
+          .@@(Middleware.logAnnotateHeaders(Header.UserAgent.name))
+          .toHttpApp
+          .runZIO {
+            Request
+              .get("/")
+              .addHeader("header", "value")
+              .addHeader(Header.UserAgent.Product("zio-http", Some("3.0.0")))
+          }
+
+        for {
+          _    <- response
+          logs <- ZTestLogger.logOutput
+          log = logs.filter(_.message() == "Oh!").head
+        } yield assertTrue(
+          log.annotations.get("header").contains("value"),
+          log.annotations.get(Header.UserAgent.name).contains("zio-http/3.0.0"),
+        )
+      },
+    )
+}
diff --git a/zio-http/src/test/scala/zio/http/RouteSpec.scala b/zio-http/src/test/scala/zio/http/RouteSpec.scala
index 8555051a53..13b4baf74a 100644
--- a/zio-http/src/test/scala/zio/http/RouteSpec.scala
+++ b/zio-http/src/test/scala/zio/http/RouteSpec.scala
@@ -16,8 +16,6 @@
 
 package zio.http
 
-import scala.collection.Seq
-
 import zio._
 import zio.test._
 
@@ -64,5 +62,21 @@ object RouteSpec extends ZIOHttpSpec {
         } yield assertTrue(cnt == 2)
       },
     ),
+    suite("error handle")(
+      test("handleErrorCauseZIO should execute a ZIO effect") {
+        val route = Method.GET / "endpoint" -> handler { (req: Request) => ZIO.fail(new Exception("hmm...")) }
+        for {
+          p <- zio.Promise.make[Exception, String]
+
+          errorHandled = route
+            .handleErrorCauseZIO(c => p.failCause(c).as(Response.internalServerError))
+
+          request = Request.get(URL.decode("/endpoint").toOption.get)
+          response <- errorHandled.toHttpApp.runZIO(request)
+          result   <- p.await.catchAllCause(c => ZIO.succeed(c.prettyPrint))
+
+        } yield assertTrue(extractStatus(response) == Status.InternalServerError, result.contains("hmm..."))
+      },
+    ),
   )
 }