diff --git a/test/acceptance/helpers.go b/test/acceptance/helpers.go
index 18b95a8..c89354b 100644
--- a/test/acceptance/helpers.go
+++ b/test/acceptance/helpers.go
@@ -69,11 +69,20 @@ func commandSummaryFor502Log(args []string) string {
 
 // runWithHTTP502Retry re-runs run() when the process exits with an error and
 // output looks like a transient Hookdeck API HTTP 502/500. Logs each retry clearly via t.Logf.
-func (r *CLIRunner) runWithHTTP502Retry(commandSummary string, run func() (stdout, stderr string, err error)) (stdout, stderr string, err error) {
+func (r *CLIRunner) runWithHTTP502Retry(commandSummary string, args []string, run func() (stdout, stderr string, err error)) (stdout, stderr string, err error) {
 	r.t.Helper()
 	var lastStdout, lastStderr string
 	var lastErr error
 	for attempt := 1; attempt <= acceptance502MaxAttempts; attempt++ {
+		if attempt > 1 {
+			// A retry re-runs the whole CLI command, which emits a fresh
+			// invocation_id. If a recording proxy captured the failed attempt's
+			// requests too, AssertTelemetryConsistent would see two invocation_ids
+			// and fail. Drop the previous attempt's recorded requests so only the
+			// final (successful) attempt remains. No-op when no recording proxy is
+			// referenced by --api-base.
+			resetRecordingProxiesForArgs(args)
+		}
 		lastStdout, lastStderr, lastErr = run()
 		if lastErr == nil || !combinedOutputLooksLikeHTTP502(lastStdout, lastStderr) {
 			return lastStdout, lastStderr, lastErr
@@ -130,11 +139,67 @@ func (p *RecordingProxy) Recorded() []RecordedRequest {
 	return out
 }
 
+// Reset clears the recorded requests. Used between CLI retries so only the
+// final (successful) attempt's requests are asserted.
+func (p *RecordingProxy) Reset() {
+	p.mu.Lock()
+	p.recorded = p.recorded[:0]
+	p.mu.Unlock()
+}
+
 // Close shuts down the proxy server.
 func (p *RecordingProxy) Close() {
+	unregisterRecordingProxy(p)
 	p.server.Close()
 }
 
+// recordingProxyByURL maps a proxy's base URL to the proxy so the CLI retry loop
+// can reset the correct proxy (found via --api-base in the command args) between
+// attempts, without every test having to wire it up.
+var (
+	recordingProxyMu    sync.Mutex
+	recordingProxyByURL = map[string]*RecordingProxy{}
+)
+
+func registerRecordingProxy(p *RecordingProxy) {
+	recordingProxyMu.Lock()
+	recordingProxyByURL[p.server.URL] = p
+	recordingProxyMu.Unlock()
+}
+
+func unregisterRecordingProxy(p *RecordingProxy) {
+	recordingProxyMu.Lock()
+	delete(recordingProxyByURL, p.server.URL)
+	recordingProxyMu.Unlock()
+}
+
+func lookupRecordingProxy(baseURL string) *RecordingProxy {
+	recordingProxyMu.Lock()
+	defer recordingProxyMu.Unlock()
+	return recordingProxyByURL[baseURL]
+}
+
+// resetRecordingProxiesForArgs clears the recorded requests of any recording
+// proxy referenced by --api-base in args. Called before a CLI retry so a failed
+// attempt's requests (which carry a different invocation_id) don't linger.
+func resetRecordingProxiesForArgs(args []string) {
+	for i, a := range args {
+		var baseURL string
+		switch {
+		case a == "--api-base" && i+1 < len(args):
+			baseURL = args[i+1]
+		case strings.HasPrefix(a, "--api-base="):
+			baseURL = strings.TrimPrefix(a, "--api-base=")
+		}
+		if baseURL == "" {
+			continue
+		}
+		if p := lookupRecordingProxy(baseURL); p != nil {
+			p.Reset()
+		}
+	}
+}
+
 // StartRecordingProxy starts an httptest.Server that acts as a reverse proxy to
 // upstreamBase (e.g. https://api.hookdeck.com). Every request is recorded
 // (method, path, X-Hookdeck-CLI-Telemetry) and then forwarded to the upstream;
@@ -200,6 +265,7 @@ func StartRecordingProxy(t *testing.T, upstreamBase string) *RecordingProxy {
 		_, _ = io.Copy(w, resp.Body)
 	}))
 
+	registerRecordingProxy(p)
 	return p
 }
 
@@ -432,7 +498,7 @@ func (r *CLIRunner) Run(args ...string) (stdout, stderr string, err error) {
 	r.t.Helper()
 
 	summary := commandSummaryFor502Log(args)
-	return r.runWithHTTP502Retry(summary, func() (string, string, error) {
+	return r.runWithHTTP502Retry(summary, args, func() (string, string, error) {
 		mainGoPath := filepath.Join(r.projectRoot, "main.go")
 		cmdArgs := append([]string{"run", mainGoPath}, args...)
 		cmd := exec.Command("go", cmdArgs...)
@@ -455,7 +521,7 @@ func (r *CLIRunner) RunWithEnv(extraEnv map[string]string, args ...string) (stdo
 	r.t.Helper()
 
 	summary := commandSummaryFor502Log(args)
-	return r.runWithHTTP502Retry(summary, func() (string, string, error) {
+	return r.runWithHTTP502Retry(summary, args, func() (string, string, error) {
 		env := os.Environ()
 		if r.configPath != "" {
 			env = appendEnvOverride(env, "HOOKDECK_CONFIG_FILE", r.configPath)
@@ -687,7 +753,7 @@ func (r *CLIRunner) RunFromCwd(args ...string) (stdout, stderr string, err error
 	}
 
 	summary := commandSummaryFor502Log(args)
-	return r.runWithHTTP502Retry(summary, func() (string, string, error) {
+	return r.runWithHTTP502Retry(summary, args, func() (string, string, error) {
 		cmd := exec.Command(tmpBinary, args...)
 		if r.configPath != "" {
 			cmd.Env = appendEnvOverride(os.Environ(), "HOOKDECK_CONFIG_FILE", r.configPath)
@@ -846,10 +912,10 @@ type Request struct {
 
 // Attempt represents a Hookdeck attempt for testing
 type Attempt struct {
-	ID           string `json:"id"`
-	EventID      string `json:"event_id"`
-	AttemptNumber int   `json:"attempt_number"`
-	Status       string `json:"status"`
+	ID            string `json:"id"`
+	EventID       string `json:"event_id"`
+	AttemptNumber int    `json:"attempt_number"`
+	Status        string `json:"status"`
 }
 
 // createTestConnection creates a basic test connection and returns its ID
diff --git a/test/acceptance/helpers_retry_test.go b/test/acceptance/helpers_retry_test.go
new file mode 100644
index 0000000..d770d10
--- /dev/null
+++ b/test/acceptance/helpers_retry_test.go
@@ -0,0 +1,68 @@
+//go:build telemetry
+
+package acceptance
+
+import (
+	"errors"
+	"fmt"
+	"net/http"
+	"net/http/httptest"
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+// TestRunWithHTTP502RetryResetsRecordingProxy is a deterministic regression test
+// for the acceptance-telemetry flake: when a CLI command hit a transient 502 and
+// was retried, the recording proxy kept the failed attempt's requests (with one
+// invocation_id) alongside the successful retry's (with a different invocation_id),
+// so AssertTelemetryConsistent failed. The retry now resets the proxy between
+// attempts, so only the final attempt's requests remain.
+//
+// It uses a fake upstream and a simulated CLI (no live API), so it never flakes.
+func TestRunWithHTTP502RetryResetsRecordingProxy(t *testing.T) {
+	upstream := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusOK)
+	}))
+	defer upstream.Close()
+
+	proxy := StartRecordingProxy(t, upstream.URL)
+	defer proxy.Close()
+
+	args := []string{"--api-base", proxy.URL(), "gateway", "connection", "list"}
+	r := &CLIRunner{t: t}
+
+	// Simulate the CLI: each attempt is a fresh process with its own invocation_id.
+	// Attempt 1 makes a request then reports a transient 502; attempt 2 succeeds.
+	attempt := 0
+	run := func() (string, string, error) {
+		attempt++
+		makeProxiedTelemetryRequest(t, proxy.URL(), fmt.Sprintf("inv-%d", attempt), "hookdeck gateway connection list")
+		if attempt == 1 {
+			return "", "error code: 502", errors.New("exit status 1")
+		}
+		return "ok", "", nil
+	}
+
+	_, _, err := r.runWithHTTP502Retry("gateway connection list", args, run)
+	require.NoError(t, err)
+	require.Equal(t, 2, attempt, "should have retried exactly once")
+
+	recorded := proxy.Recorded()
+	require.Len(t, recorded, 1, "only the successful retry's request should remain after the reset (got %d)", len(recorded))
+	// The remaining requests must be internally consistent — this is what the flake broke.
+	AssertTelemetryConsistent(t, recorded, "hookdeck gateway connection list")
+}
+
+// makeProxiedTelemetryRequest issues one request through the proxy carrying an
+// X-Hookdeck-CLI-Telemetry header with the given invocation_id and command_path.
+func makeProxiedTelemetryRequest(t *testing.T, proxyURL, invocationID, commandPath string) {
+	t.Helper()
+	req, err := http.NewRequest(http.MethodGet, proxyURL+"/2025-07-01/connections", nil)
+	require.NoError(t, err)
+	req.Header.Set("X-Hookdeck-CLI-Telemetry",
+		fmt.Sprintf(`{"command_path":%q,"invocation_id":%q}`, commandPath, invocationID))
+	resp, err := http.DefaultClient.Do(req)
+	require.NoError(t, err)
+	require.NoError(t, resp.Body.Close())
+}