diff --git a/internal/outpost/ak/api.go b/internal/outpost/ak/api.go
index b6616ef2e..b690e1cba 100644
--- a/internal/outpost/ak/api.go
+++ b/internal/outpost/ak/api.go
@@ -47,7 +47,7 @@ func NewAPIController(akURL url.URL, token string) *APIController {
 	config.Host = akURL.Host
 	config.Scheme = akURL.Scheme
 	config.HTTPClient = &http.Client{
-		Transport: NewTracingTransport(GetTLSTransport()),
+		Transport: NewTracingTransport(context.TODO(), GetTLSTransport()),
 	}
 	config.AddDefaultHeader("Authorization", fmt.Sprintf("Bearer %s", token))
 
diff --git a/internal/outpost/ak/tracing.go b/internal/outpost/ak/tracing.go
index 54e0871e1..dd3bf40d6 100644
--- a/internal/outpost/ak/tracing.go
+++ b/internal/outpost/ak/tracing.go
@@ -1,6 +1,7 @@
 package ak
 
 import (
+	"context"
 	"net/http"
 
 	"github.com/getsentry/sentry-go"
@@ -8,14 +9,15 @@ import (
 
 type tracingTransport struct {
 	inner http.RoundTripper
+	ctx   context.Context
 }
 
-func NewTracingTransport(inner http.RoundTripper) *tracingTransport {
-	return &tracingTransport{inner}
+func NewTracingTransport(ctx context.Context, inner http.RoundTripper) *tracingTransport {
+	return &tracingTransport{inner, ctx}
 }
 
 func (tt *tracingTransport) RoundTrip(r *http.Request) (*http.Response, error) {
-	span := sentry.StartSpan(r.Context(), "authentik.go.http_request")
+	span := sentry.StartSpan(tt.ctx, "authentik.go.http_request")
 	span.SetTag("url", r.URL.String())
 	span.SetTag("method", r.Method)
 	defer span.Finish()
diff --git a/internal/outpost/flow.go b/internal/outpost/flow.go
index 2bc444751..832e4fd51 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.NewTracingTransport(ak.GetTLSTransport()),
+		Transport: ak.NewTracingTransport(ctx, ak.GetTLSTransport()),
 	}
 	apiClient := api.NewAPIClient(config)
 	return &FlowExecutor{