diff --git a/components/egress/main.go b/components/egress/main.go
index 347e87869..d74c98c23 100644
--- a/components/egress/main.go
+++ b/components/egress/main.go
@@ -50,6 +50,11 @@ func main() {
 	ctx = withLogger(ctx)
 	defer log.Logger.Sync()
 
+	// Erase any stale mitmproxy CA left on the shared volume by a previous
+	// egress generation so the agent's bootstrap wait-loop blocks for this
+	// generation's export. See PurgeStaleExportedCA / upstream issue #1370.
+	mitmproxy.PurgeStaleExportedCA()
+
 	otelShutdown, err := telemetry.Init(ctx)
 	if err != nil {
 		log.Warnf("OpenTelemetry metrics disabled (continuing without OTLP): %v", err)
diff --git a/components/egress/pkg/mitmproxy/cacert_export.go b/components/egress/pkg/mitmproxy/cacert_export.go
index 258767aa8..3fc235dd4 100644
--- a/components/egress/pkg/mitmproxy/cacert_export.go
+++ b/components/egress/pkg/mitmproxy/cacert_export.go
@@ -62,6 +62,40 @@ func waitMitmCACertPath(confDirEnv, home string) (string, error) {
 	return "", fmt.Errorf("mitmproxy CA not found after %v (tried: %v)", waitCACert, cands)
 }
 
+// PurgeStaleExportedCA removes any mitmproxy-ca-cert.pem left on the shared
+// volume by a previous generation of this egress container. mitmproxy's CA
+// lives in the egress container's ephemeral confdir, so an egress container
+// restart rotates the CA while the previous public cert is still on the
+// (pod-scoped) shared volume; without this purge, an agent container starting
+// alongside us would pass its bootstrap readiness check on the stale file
+// and install a CA that no longer matches what mitmproxy will sign with.
+// See upstream issue #1370. Must be called as early as possible in main().
+func PurgeStaleExportedCA() {
+	if !constants.IsTruthy(os.Getenv(constants.EnvMitmproxyTransparent)) {
+		return
+	}
+	purgeStaleExportedCAFrom(constants.OpenSandboxRootDir)
+}
+
+// purgeStaleExportedCAFrom is the testable core of PurgeStaleExportedCA.
+func purgeStaleExportedCAFrom(rootDir string) {
+	path := filepath.Join(rootDir, mitmCACertName)
+	err := os.Remove(path)
+	switch {
+	case err == nil:
+		// warn: on first pod startup this file should not exist; its presence
+		// means the egress container (or process) has restarted, which is
+		// useful signal when diagnosing HTTPS-from-agent problems.
+		log.Warnf("[mitmproxy] removed stale exported CA at %s (previous egress generation left it behind; see upstream issue #1370)", path)
+	case os.IsNotExist(err):
+		// Common on first pod startup.
+	default:
+		// Non-fatal: SyncRootCA will overwrite the file. But on the race
+		// path the agent may still grab the old contents before we do.
+		log.Warnf("[mitmproxy] failed to remove stale exported CA at %s: %v", path, err)
+	}
+}
+
 func SyncRootCA(confDirEnv, home string) error {
 	src, err := waitMitmCACertPath(confDirEnv, home)
 	if err != nil {
diff --git a/components/egress/pkg/mitmproxy/cacert_export_test.go b/components/egress/pkg/mitmproxy/cacert_export_test.go
index 13731c759..157d07936 100644
--- a/components/egress/pkg/mitmproxy/cacert_export_test.go
+++ b/components/egress/pkg/mitmproxy/cacert_export_test.go
@@ -15,6 +15,7 @@
 package mitmproxy
 
 import (
+	"os"
 	"path/filepath"
 	"testing"
 
@@ -33,3 +34,41 @@ func TestCandidateCACertPaths(t *testing.T) {
 		filepath.Join(h, ".mitmproxy", mitmCACertName),
 	}, got)
 }
+
+func TestPurgeStaleExportedCAFrom_RemovesExistingFile(t *testing.T) {
+	root := t.TempDir()
+	path := filepath.Join(root, mitmCACertName)
+	require.NoError(t, os.WriteFile(path, []byte("stale-ca"), 0o644))
+
+	purgeStaleExportedCAFrom(root)
+
+	_, err := os.Stat(path)
+	require.True(t, os.IsNotExist(err), "expected file to be removed, got err=%v", err)
+}
+
+func TestPurgeStaleExportedCAFrom_NoFileIsNoOp(t *testing.T) {
+	root := t.TempDir()
+	// No file present; must not panic and must not create anything.
+	purgeStaleExportedCAFrom(root)
+
+	entries, err := os.ReadDir(root)
+	require.NoError(t, err)
+	require.Empty(t, entries)
+}
+
+func TestPurgeStaleExportedCAFrom_LeavesUnrelatedFiles(t *testing.T) {
+	root := t.TempDir()
+	stale := filepath.Join(root, mitmCACertName)
+	require.NoError(t, os.WriteFile(stale, []byte("stale-ca"), 0o644))
+
+	// A sibling file that must survive (e.g. the agent's merged bundle).
+	other := filepath.Join(root, "merged-ca-certificates.pem")
+	require.NoError(t, os.WriteFile(other, []byte("merged"), 0o644))
+
+	purgeStaleExportedCAFrom(root)
+
+	_, err := os.Stat(stale)
+	require.True(t, os.IsNotExist(err))
+	_, err = os.Stat(other)
+	require.NoError(t, err)
+}