diff --git a/controller/controller.go b/controller/controller.go
index 8d058b02..119ed732 100644
--- a/controller/controller.go
+++ b/controller/controller.go
@@ -14,7 +14,7 @@ import (
 	"github.com/brave/go-sync/datastore"
 	syncMiddleware "github.com/brave/go-sync/middleware"
 	"github.com/brave/go-sync/schema/protobuf/sync_pb"
-	"github.com/go-chi/chi"
+	"github.com/go-chi/chi/v5"
 	"github.com/rs/zerolog/log"
 	"google.golang.org/protobuf/proto"
 )
diff --git a/go.mod b/go.mod
index 1d7cd39a..61eff765 100644
--- a/go.mod
+++ b/go.mod
@@ -6,7 +6,6 @@ require (
 	github.com/aws/aws-sdk-go v1.45.7
 	github.com/brave-intl/bat-go v0.5.1
 	github.com/getsentry/sentry-go v0.24.0
-	github.com/go-chi/chi v4.1.2+incompatible
 	github.com/go-chi/chi/v5 v5.0.10
 	github.com/go-redis/redis/v8 v8.11.5
 	github.com/prometheus/client_golang v1.16.0
@@ -22,6 +21,7 @@ require (
 	github.com/cespare/xxhash/v2 v2.2.0 // indirect
 	github.com/davecgh/go-spew v1.1.1 // indirect
 	github.com/dgryski/go-rendezvous v0.0.0-20200823014737-9f7001d12a5f // indirect
+	github.com/go-chi/chi v4.1.2+incompatible // indirect
 	github.com/golang/protobuf v1.5.3 // indirect
 	github.com/gomodule/redigo v2.0.0+incompatible // indirect
 	github.com/hashicorp/golang-lru v0.5.4 // indirect
diff --git a/go.sum b/go.sum
index 7c12d415..c2709bc0 100644
--- a/go.sum
+++ b/go.sum
@@ -168,8 +168,6 @@ github.com/aws/aws-sdk-go v1.27.0/go.mod h1:KmX6BPdI08NWTb3/sm4ZGu5ShLoqVDhKgpiN
 github.com/aws/aws-sdk-go v1.30.27/go.mod h1:5zCpMtNQVjRREroY7sYe8lOMRSxkhG6MZveU8YkpAk0=
 github.com/aws/aws-sdk-go v1.34.28/go.mod h1:H7NKnBqNVzoTJpGfLrQkkD+ytBA93eiDYi/+8rV9s48=
 github.com/aws/aws-sdk-go v1.37.19/go.mod h1:hcU610XS61/+aQV88ixoOzUoG7v3b31pl2zKMmprdro=
-github.com/aws/aws-sdk-go v1.45.6 h1:Y2isQQBZsnO15dzUQo9YQRThtHgrV200XCH05BRHVJI=
-github.com/aws/aws-sdk-go v1.45.6/go.mod h1:aVsgQcEevwlmQ7qHE9I3h+dtQgpqhFB+i8Phjh7fkwI=
 github.com/aws/aws-sdk-go v1.45.7 h1:k4QsvWZhm8409TYeRuTV1P6+j3lLKoe+giFA/j3VAps=
 github.com/aws/aws-sdk-go v1.45.7/go.mod h1:aVsgQcEevwlmQ7qHE9I3h+dtQgpqhFB+i8Phjh7fkwI=
 github.com/aws/aws-sdk-go-v2 v0.18.0/go.mod h1:JWVYvqSMppoMJC0x5wdwiImzgXTI9FuZwxzkQq9wy+g=
@@ -357,6 +355,7 @@ github.com/go-asn1-ber/asn1-ber v1.5.1/go.mod h1:hEBeB/ic+5LoWskz+yKT7vGhhPYkPro
 github.com/go-check/check v0.0.0-20180628173108-788fd7840127/go.mod h1:9ES+weclKsC9YodN5RgxqK/VD9HM9JsCSh7rNhMZE98=
 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/v5 v5.0.10 h1:rLz5avzKpjqxrYwXNfmjkrYYXOyLJd37pz53UFHC6vk=
 github.com/go-chi/chi/v5 v5.0.10/go.mod h1:DslCQbL2OYiznFReuXYUmQ2hGd1aDpCnlMNITLSKoi8=
 github.com/go-chi/cors v1.2.0/go.mod h1:sSbTewc+6wYHBBCW7ytsFSn836hqM7JxpglAy2Vzc58=
 github.com/go-errors/errors v1.0.1/go.mod h1:f4zRHt4oKfwPJE5k8C9vpYG+aDHdBFUsgrm6/TyX73Q=
diff --git a/server/server.go b/server/server.go
index 47e6d147..ab7e0955 100644
--- a/server/server.go
+++ b/server/server.go
@@ -3,6 +3,7 @@ package server
 import (
 	"context"
 	"fmt"
+	"net"
 	"net/http"
 	_ "net/http/pprof" // pprof magic
 	"os"
@@ -20,8 +21,8 @@ import (
 	"github.com/brave/go-sync/datastore"
 	"github.com/brave/go-sync/middleware"
 	sentry "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/rs/zerolog"
 	"github.com/rs/zerolog/hlog"
 	"github.com/rs/zerolog/log"
@@ -34,6 +35,8 @@ var (
 	healthCheckActive = true
 )
 
+type baseCtxFunc = func(net.Listener) context.Context
+
 func setupLogger(ctx context.Context) (context.Context, *zerolog.Logger) {
 	ctx = context.WithValue(ctx, appctx.EnvironmentCTXKey, os.Getenv("ENV"))
 	ctx = context.WithValue(ctx, appctx.LogLevelCTXKey, zerolog.WarnLevel)
@@ -104,6 +107,12 @@ func setupRouter(ctx context.Context, logger *zerolog.Logger) (context.Context,
 	return ctx, r
 }
 
+func setupBaseCtx(ctx context.Context) baseCtxFunc {
+	return func(_ net.Listener) context.Context {
+		return ctx
+	}
+}
+
 // StartServer starts the translate proxy server on port 8195
 func StartServer() {
 	serverCtx, logger := setupLogger(context.Background())
@@ -126,7 +135,11 @@ func StartServer() {
 	serverCtx, r := setupRouter(serverCtx, logger)
 
 	port := ":8295"
-	srv := http.Server{Addr: port, Handler: chi.ServerBaseContext(serverCtx, r)}
+	srv := http.Server{
+		Addr:        port,
+		Handler:     r,
+		BaseContext: setupBaseCtx(serverCtx),
+	}
 
 	sig := make(chan os.Signal, 1)
 	signal.Notify(sig, syscall.SIGTERM)
diff --git a/server/server_test.go b/server/server_test.go
index 84923fe3..22f4ad56 100644
--- a/server/server_test.go
+++ b/server/server_test.go
@@ -8,16 +8,18 @@ import (
 	"testing"
 
 	"github.com/brave/go-sync/server"
-	"github.com/go-chi/chi"
+	"github.com/go-chi/chi/v5"
 	"github.com/stretchr/testify/assert"
 )
 
-var handler http.Handler
+var (
+	mux       *chi.Mux
+	serverCtx context.Context
+)
 
 func init() {
 	testCtx, logger := server.SetupLogger(context.Background())
-	serverCtx, mux := server.SetupRouter(testCtx, logger)
-	handler = chi.ServerBaseContext(serverCtx, mux)
+	serverCtx, mux = server.SetupRouter(testCtx, logger)
 }
 
 func TestPing(t *testing.T) {
@@ -25,7 +27,7 @@ func TestPing(t *testing.T) {
 	assert.Nil(t, err)
 
 	rr := httptest.NewRecorder()
-	handler.ServeHTTP(rr, req)
+	mux.ServeHTTP(rr, req.WithContext(serverCtx))
 	assert.Equal(t, http.StatusOK, rr.Code)
 
 	expected := "."
@@ -39,7 +41,7 @@ func TestCommand(t *testing.T) {
 	assert.Nil(t, err)
 
 	rr := httptest.NewRecorder()
-	handler.ServeHTTP(rr, req)
+	mux.ServeHTTP(rr, req.WithContext(serverCtx))
 	assert.Equal(t, http.StatusUnauthorized, rr.Code)
 	assert.NotEmpty(t, rr.Result().Header.Get("Sane-Time-Millis"))
 }