diff --git a/integration/autoupdate/tools/updater_test.go b/integration/autoupdate/tools/updater_test.go
index 0ef2eabb4aa41..47b2e3460fa23 100644
--- a/integration/autoupdate/tools/updater_test.go
+++ b/integration/autoupdate/tools/updater_test.go
@@ -69,9 +69,7 @@ func TestUpdate(t *testing.T) {
 	out, err := cmd.Output()
 	require.NoError(t, err)
 
-	matches := pattern.FindStringSubmatch(string(out))
-	require.Len(t, matches, 2)
-	require.Equal(t, testVersions[0], matches[1])
+	matchVersion(t, string(out), testVersions[0])
 
 	// Execute version command again with setting the new version which must
 	// trigger re-execution of the same command after downloading requested version.
@@ -83,9 +81,7 @@ func TestUpdate(t *testing.T) {
 	out, err = cmd.Output()
 	require.NoError(t, err)
 
-	matches = pattern.FindStringSubmatch(string(out))
-	require.Len(t, matches, 2)
-	require.Equal(t, testVersions[1], matches[1])
+	matchVersion(t, string(out), testVersions[1])
 }
 
 // TestParallelUpdate launches multiple updater commands in parallel while defining a new version.
@@ -258,9 +254,7 @@ func TestUpdateForOSSBuild(t *testing.T) {
 	out, err := cmd.Output()
 	require.NoError(t, err)
 
-	matches := pattern.FindStringSubmatch(string(out))
-	require.Len(t, matches, 2)
-	require.Equal(t, testVersions[0], matches[1])
+	matchVersion(t, string(out), testVersions[0])
 
 	// Next update is set with the base URL env variable, must download new version.
 	t.Setenv(autoupdate.BaseURLEnvVar, baseURL)
@@ -272,7 +266,12 @@ func TestUpdateForOSSBuild(t *testing.T) {
 	out, err = cmd.Output()
 	require.NoError(t, err)
 
-	matches = pattern.FindStringSubmatch(string(out))
+	matchVersion(t, string(out), testVersions[1])
+}
+
+func matchVersion(t *testing.T, output string, version string) {
+	t.Helper()
+	matches := pattern.FindStringSubmatch(output)
 	require.Len(t, matches, 2)
-	require.Equal(t, testVersions[1], matches[1])
+	require.Equal(t, version, matches[1])
 }
diff --git a/integration/autoupdate/tools/updater_tsh_test.go b/integration/autoupdate/tools/updater_tsh_test.go
index 78d674002efd4..5c92ac07fb080 100644
--- a/integration/autoupdate/tools/updater_tsh_test.go
+++ b/integration/autoupdate/tools/updater_tsh_test.go
@@ -105,9 +105,7 @@ func TestAliasLoginWithUpdater(t *testing.T) {
 	cmd = exec.CommandContext(ctx, tshPath, "version")
 	out, err = cmd.Output()
 	require.NoError(t, err)
-	matches := pattern.FindStringSubmatch(string(out))
-	require.Len(t, matches, 2)
-	require.Equal(t, testVersions[1], matches[1])
+	matchVersion(t, string(out), testVersions[1])
 
 	// Verifies that version commands shows version re-executed from.
 	require.Contains(t, string(out), fmt.Sprintf("Re-executed from version: %s", testVersions[0]))
@@ -152,9 +150,7 @@ func TestLoginWithUpdaterAndProfile(t *testing.T) {
 	cmd = exec.CommandContext(ctx, tshPath, "version")
 	out, err := cmd.Output()
 	require.NoError(t, err)
-	matches := pattern.FindStringSubmatch(string(out))
-	require.Len(t, matches, 2)
-	require.Equal(t, testVersions[1], matches[1])
+	matchVersion(t, string(out), testVersions[1])
 }
 
 // TestLoginWithDisabledUpdateInProfile runs test cluster with enabled managed updates for client tools,
@@ -188,9 +184,7 @@ func TestLoginWithDisabledUpdateInProfile(t *testing.T) {
 	out, err := cmd.Output()
 	require.NoError(t, err)
 	// Check the version.
-	matches := pattern.FindStringSubmatch(string(out))
-	require.Len(t, matches, 2)
-	require.Equal(t, testVersions[1], matches[1])
+	matchVersion(t, string(out), testVersions[1])
 	// Unset the version after update process.
 	require.NoError(t, os.Unsetenv("TELEPORT_TOOLS_VERSION"))
 
@@ -208,10 +202,7 @@ func TestLoginWithDisabledUpdateInProfile(t *testing.T) {
 	out, err = cmd.Output()
 	require.NoError(t, err)
 	// Check the version.
-	matches = pattern.FindStringSubmatch(string(out))
-	require.Len(t, matches, 2)
-	fmt.Println(string(out))
-	require.Equal(t, testVersions[0], matches[1])
+	matchVersion(t, string(out), testVersions[0])
 }
 
 // TestLoginWithDisabledUpdateForcedByEnv verifies that on disabled cluster we are still
@@ -253,10 +244,7 @@ func TestLoginWithDisabledUpdateForcedByEnv(t *testing.T) {
 	out, err := cmd.Output()
 	require.NoError(t, err)
 	// Check that version is used that requested from env variable.
-	matches := pattern.FindStringSubmatch(string(out))
-	require.Len(t, matches, 2)
-	fmt.Println(string(out))
-	require.Equal(t, testVersions[1], matches[1])
+	matchVersion(t, string(out), testVersions[1])
 	// Unset the version after update process.
 	require.NoError(t, os.Unsetenv("TELEPORT_TOOLS_VERSION"))
 
@@ -266,10 +254,39 @@ func TestLoginWithDisabledUpdateForcedByEnv(t *testing.T) {
 	cmd = exec.CommandContext(ctx, tshPath, "version")
 	out, err = cmd.Output()
 	require.NoError(t, err)
-	matches = pattern.FindStringSubmatch(string(out))
-	require.Len(t, matches, 2)
-	fmt.Println(string(out))
-	require.Equal(t, testVersions[0], matches[1])
+	matchVersion(t, string(out), testVersions[0])
+}
+
+// TestMigratedUpdateNotReExec verifies that the version is migrated without errors,
+// and that the previous version of the updated tools is ignored.
+func TestMigratedUpdateNotReExec(t *testing.T) {
+	testToolsDir := t.TempDir()
+	t.Setenv(types.HomeEnvVar, testToolsDir)
+	ctx := context.Background()
+
+	// Fetch compiled test binary with updater logic and install to $TELEPORT_HOME.
+	updater := tools.NewUpdater(
+		testToolsDir,
+		testVersions[0],
+		tools.WithBaseURL(baseURL),
+	)
+	err := updater.Update(ctx, testVersions[0])
+	require.NoError(t, err)
+
+	tshPath, err := updater.ToolPath("tsh", testVersions[0])
+	require.NoError(t, err)
+
+	require.NoError(t, os.MkdirAll(filepath.Join(testToolsDir, "bin"), 0755))
+	require.NoError(t, os.WriteFile(filepath.Join(testToolsDir, "bin", "tsh"), []byte("#!/bin/sh\n echo 'Teleport v5.5.5 git'\n"), 0755))
+
+	// Verify that the installed version is equal to requested one.
+	cmd := exec.CommandContext(ctx, tshPath, "version")
+	out, err := cmd.Output()
+	require.NoError(t, err)
+
+	require.NotContains(t, string(out), "version check failed")
+
+	matchVersion(t, string(out), testVersions[0])
 }
 
 func bootstrapTestServer(t *testing.T) (*service.TeleportProcess, string, string) {
diff --git a/lib/autoupdate/tools/updater.go b/lib/autoupdate/tools/updater.go
index 1d470e586d131..348d6f581c7bc 100644
--- a/lib/autoupdate/tools/updater.go
+++ b/lib/autoupdate/tools/updater.go
@@ -202,7 +202,7 @@ func (u *Updater) CheckLocal(ctx context.Context, profileName string) (resp *Upd
 		}
 	}
 
-	return &UpdateResponse{Version: toolsVersion, ReExec: true}, nil
+	return &UpdateResponse{Version: toolsVersion, ReExec: false}, nil
 }
 
 // CheckRemote first checks the version set by the environment variable. If not set or disabled,