diff --git a/.gitignore b/.gitignore
index d8ec889b..3c7c8490 100644
--- a/.gitignore
+++ b/.gitignore
@@ -4,7 +4,10 @@
 *.dll
 *.so
 *.dylib
+
+# Build output
 main
+go-update
 
 # Test binary, build with `go test -c`
 *.test
diff --git a/controller/controller.go b/controller/controller.go
index cc6fd402..3f64d6ac 100644
--- a/controller/controller.go
+++ b/controller/controller.go
@@ -19,7 +19,7 @@ import (
 	"github.com/brave/go-update/omaha"
 	"github.com/brave/go-update/omaha/protocol"
 	"github.com/getsentry/sentry-go"
-	"github.com/go-chi/chi"
+	"github.com/go-chi/chi/v5"
 	"github.com/pressly/lg"
 )
 
diff --git a/go.mod b/go.mod
index 65ac9995..0286f976 100644
--- a/go.mod
+++ b/go.mod
@@ -6,7 +6,7 @@ require (
 	github.com/aws/aws-sdk-go v1.55.7
 	github.com/brave-intl/bat-go v0.1.0
 	github.com/getsentry/sentry-go v0.32.0
-	github.com/go-chi/chi v4.1.2+incompatible
+	github.com/go-chi/chi/v5 v5.0.12
 	github.com/go-playground/validator/v10 v10.26.0
 	github.com/pressly/lg v1.1.1
 	github.com/sirupsen/logrus v1.9.3
@@ -20,6 +20,7 @@ require (
 	github.com/davecgh/go-spew v1.1.1 // indirect
 	github.com/gabriel-vasile/mimetype v1.4.8 // indirect
 	github.com/getsentry/raven-go v0.2.1-0.20190619092523-5c24d5110e0e // indirect
+	github.com/go-chi/chi v1.5.5 // indirect
 	github.com/go-playground/locales v0.14.1 // indirect
 	github.com/go-playground/universal-translator v0.18.1 // indirect
 	github.com/golang/protobuf v1.5.3 // indirect
diff --git a/go.sum b/go.sum
index 7f496a50..3d19792d 100644
--- a/go.sum
+++ b/go.sum
@@ -1,5 +1,3 @@
-github.com/aws/aws-sdk-go v1.55.6 h1:cSg4pvZ3m8dgYcgqB97MrcdjUmZ1BeMYKUxMMB89IPk=
-github.com/aws/aws-sdk-go v1.55.6/go.mod h1:eRwEWoyTWFMVYVQzKMNHWP5/RV4xIUGMQfXQHfHkpNU=
 github.com/aws/aws-sdk-go v1.55.7 h1:UJrkFq7es5CShfBwlWAC8DA077vp8PyVbQd3lqLiztE=
 github.com/aws/aws-sdk-go v1.55.7/go.mod h1:eRwEWoyTWFMVYVQzKMNHWP5/RV4xIUGMQfXQHfHkpNU=
 github.com/beorn7/perks v1.0.1 h1:VlbKKnNfV8bJzeqoa4cOKqO6bYr3WgKZxO8Z16+hsOM=
@@ -18,12 +16,12 @@ github.com/gabriel-vasile/mimetype v1.4.8 h1:FfZ3gj38NjllZIeJAmMhr+qKL8Wu+nOoI3G
 github.com/gabriel-vasile/mimetype v1.4.8/go.mod h1:ByKUIKGjh1ODkGM1asKUbQZOLGrPjydw3hYPU2YU9t8=
 github.com/getsentry/raven-go v0.2.1-0.20190619092523-5c24d5110e0e h1:kpHZPjNRhYcj0G1Y4NryfaoeFF/BSSPd2OwiXbzEMPo=
 github.com/getsentry/raven-go v0.2.1-0.20190619092523-5c24d5110e0e/go.mod h1:KungGk8q33+aIAZUIVWZDr2OfAEBsO49PX4NzFV5kcQ=
-github.com/getsentry/sentry-go v0.31.1 h1:ELVc0h7gwyhnXHDouXkhqTFSO5oslsRDk0++eyE0KJ4=
-github.com/getsentry/sentry-go v0.31.1/go.mod h1:CYNcMMz73YigoHljQRG+qPF+eMq8gG72XcGN/p71BAY=
 github.com/getsentry/sentry-go v0.32.0 h1:YKs+//QmwE3DcYtfKRH8/KyOOF/I6Qnx7qYGNHCGmCY=
 github.com/getsentry/sentry-go v0.32.0/go.mod h1:CYNcMMz73YigoHljQRG+qPF+eMq8gG72XcGN/p71BAY=
-github.com/go-chi/chi v4.1.2+incompatible h1:fGFk2Gmi/YKXk0OmGfBh0WgmN3XB8lVnEyNz34tQRec=
-github.com/go-chi/chi v4.1.2+incompatible/go.mod h1:eB3wogJHnLi3x/kFX2A+IbTBlXxmMeXJVKy9tTv1XzQ=
+github.com/go-chi/chi v1.5.5 h1:vOB/HbEMt9QqBqErz07QehcOKHaWFtuj87tTDVz2qXE=
+github.com/go-chi/chi v1.5.5/go.mod h1:C9JqLr3tIYjDOZpzn+BCuxY8z8vmca43EeMgyZt7irw=
+github.com/go-chi/chi/v5 v5.0.12 h1:9euLV5sTrTNTRUU9POmDUvfxyj6LAABLUcEWO+JJb4s=
+github.com/go-chi/chi/v5 v5.0.12/go.mod h1:DslCQbL2OYiznFReuXYUmQ2hGd1aDpCnlMNITLSKoi8=
 github.com/go-errors/errors v1.4.2 h1:J6MZopCL4uSllY1OfXM374weqZFFItUbrImctkmUxIA=
 github.com/go-errors/errors v1.4.2/go.mod h1:sIVyrIiJhuEF+Pj9Ebtd6P/rEYROXFi3BopGUQ5a5Og=
 github.com/go-playground/assert/v2 v2.2.0 h1:JvknZsQTYeFEAhQwI4qEt9cyV5ONwRHC+lYKSsYSR8s=
diff --git a/server/server.go b/server/server.go
index b0f2751e..7f0136d0 100644
--- a/server/server.go
+++ b/server/server.go
@@ -5,6 +5,7 @@ import (
 	"context"
 	"fmt"
 	"log"
+	"net"
 	"net/http"
 	_ "net/http/pprof" // pprof magic
 	"os"
@@ -15,8 +16,8 @@ import (
 	"github.com/brave/go-update/controller"
 	"github.com/brave/go-update/extension"
 	"github.com/getsentry/sentry-go"
-	"github.com/go-chi/chi"
-	chiware "github.com/go-chi/chi/middleware"
+	"github.com/go-chi/chi/v5"
+	chiware "github.com/go-chi/chi/v5/middleware"
 	"github.com/pressly/lg"
 	"github.com/sirupsen/logrus"
 )
@@ -76,7 +77,11 @@ func StartServer() {
 	serverCtx, r := setupRouter(serverCtx, logger, false)
 	port := ":8192"
 	fmt.Printf("Starting server: http://localhost%s", port)
-	srv := http.Server{Addr: port, Handler: chi.ServerBaseContext(serverCtx, r)}
+	srv := http.Server{
+		Addr:        port,
+		Handler:     r,
+		BaseContext: func(_ net.Listener) context.Context { return serverCtx },
+	}
 	err := srv.ListenAndServe()
 	if err != nil {
 		sentry.CaptureException(err)
diff --git a/server/server_test.go b/server/server_test.go
index a46cd1e7..28099e1a 100644
--- a/server/server_test.go
+++ b/server/server_test.go
@@ -17,7 +17,7 @@ import (
 	"github.com/brave/go-update/controller"
 	"github.com/brave/go-update/extension"
 	"github.com/brave/go-update/extension/extensiontest"
-	"github.com/go-chi/chi"
+	"github.com/pressly/lg"
 	"github.com/stretchr/testify/assert"
 )
 
@@ -59,7 +59,15 @@ func init() {
 	controller.AllExtensionsMap.StoreExtensions(&extension.OfferedExtensions)
 	controller.ExtensionUpdaterTimeout = time.Millisecond * 1
 	testCtx, logger := setupLogger(context.Background())
-	handler = chi.ServerBaseContext(setupRouter(testCtx, logger, true))
+	_, router := setupRouter(testCtx, logger, true)
+
+	// Create a middleware that adds the context with logger to each request
+	handler = http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		// Add the logger to the context
+		ctx := lg.WithLoggerContext(r.Context(), logger)
+		router.ServeHTTP(w, r.WithContext(ctx))
+	})
+
 	controller.RefreshExtensionsTicker(func() {
 		count++
 		if count == 1 {