diff --git a/internal/outpost/ak/api.go b/internal/outpost/ak/api.go
index 79465eadc..26a02b16c 100644
--- a/internal/outpost/ak/api.go
+++ b/internal/outpost/ak/api.go
@@ -44,7 +44,7 @@ func NewAPIController(akURL url.URL, token string) *APIController {
 	config.Host = akURL.Host
 	config.Scheme = akURL.Scheme
 	config.HTTPClient = &http.Client{
-		Transport: GetTLSTransport(),
+		Transport: NewTracingTransport(GetTLSTransport()),
 	}
 	config.AddDefaultHeader("Authorization", fmt.Sprintf("Bearer %s", token))
 
diff --git a/internal/outpost/ak/tracing.go b/internal/outpost/ak/tracing.go
new file mode 100644
index 000000000..54e0871e1
--- /dev/null
+++ b/internal/outpost/ak/tracing.go
@@ -0,0 +1,23 @@
+package ak
+
+import (
+	"net/http"
+
+	"github.com/getsentry/sentry-go"
+)
+
+type tracingTransport struct {
+	inner http.RoundTripper
+}
+
+func NewTracingTransport(inner http.RoundTripper) *tracingTransport {
+	return &tracingTransport{inner}
+}
+
+func (tt *tracingTransport) RoundTrip(r *http.Request) (*http.Response, error) {
+	span := sentry.StartSpan(r.Context(), "authentik.go.http_request")
+	span.SetTag("url", r.URL.String())
+	span.SetTag("method", r.Method)
+	defer span.Finish()
+	return tt.inner.RoundTrip(r.WithContext(span.Context()))
+}
diff --git a/internal/outpost/flow.go b/internal/outpost/flow.go
index 0ffbdabf6..dbcd47bb1 100644
--- a/internal/outpost/flow.go
+++ b/internal/outpost/flow.go
@@ -61,7 +61,7 @@ func NewFlowExecutor(ctx context.Context, flowSlug string, refConfig *api.Config
 	config.UserAgent = constants.OutpostUserAgent()
 	config.HTTPClient = &http.Client{
 		Jar:       jar,
-		Transport: ak.GetTLSTransport(),
+		Transport: ak.NewTracingTransport(ak.GetTLSTransport()),
 	}
 	apiClient := api.NewAPIClient(config)
 	return &FlowExecutor{