diff --git a/integration/autoupdate/tools/updater_tsh_test.go b/integration/autoupdate/tools/updater_tsh_test.go
index 01b9ca7679a42..b2372683b6c5a 100644
--- a/integration/autoupdate/tools/updater_tsh_test.go
+++ b/integration/autoupdate/tools/updater_tsh_test.go
@@ -143,4 +143,7 @@ func TestAliasLoginWithUpdater(t *testing.T) {
 	matches := pattern.FindStringSubmatch(string(out))
 	require.Len(t, matches, 2)
 	require.Equal(t, testVersions[1], matches[1])
+
+	// Verifies that version commands shows version re-executed from.
+	require.Contains(t, string(out), fmt.Sprintf("Re-executed from version: %s", testVersions[0]))
 }
diff --git a/lib/autoupdate/tools/updater.go b/lib/autoupdate/tools/updater.go
index eded34049e473..b236324c81d88 100644
--- a/lib/autoupdate/tools/updater.go
+++ b/lib/autoupdate/tools/updater.go
@@ -50,6 +50,9 @@ import (
 const (
 	// teleportToolsVersionEnv is environment name for requesting specific version for update.
 	teleportToolsVersionEnv = "TELEPORT_TOOLS_VERSION"
+	// teleportToolsVersionReExecEnv is internal environment name for transferring original
+	// version to re-executed ones.
+	teleportToolsVersionReExecEnv = "TELEPORT_TOOLS_VERSION_REEXEC"
 	// reservedFreeDisk is the predefined amount of free disk space (in bytes) required
 	// to remain available after downloading archives.
 	reservedFreeDisk = 10 * 1024 * 1024 // 10 Mb
@@ -345,6 +348,9 @@ func (u *Updater) Exec(args []string) (int, error) {
 	if err := os.Unsetenv(teleportToolsVersionEnv); err != nil {
 		return 0, trace.Wrap(err)
 	}
+	if err := os.Unsetenv(teleportToolsVersionReExecEnv); err != nil {
+		return 0, trace.Wrap(err)
+	}
 
 	env := os.Environ()
 	executablePath, err := os.Executable()
@@ -354,6 +360,7 @@ func (u *Updater) Exec(args []string) (int, error) {
 	if path == executablePath {
 		env = append(env, teleportToolsVersionEnv+"=off")
 	}
+	env = append(env, fmt.Sprintf("%s=%s", teleportToolsVersionReExecEnv, u.localVersion))
 
 	if runtime.GOOS == constants.WindowsOS {
 		cmd := exec.Command(path, args...)
diff --git a/lib/autoupdate/tools/utils.go b/lib/autoupdate/tools/utils.go
index 6da7974bd5793..e158ef534169a 100644
--- a/lib/autoupdate/tools/utils.go
+++ b/lib/autoupdate/tools/utils.go
@@ -120,6 +120,19 @@ func CheckToolVersion(toolsDir string) (string, error) {
 	return "", trace.BadParameter("unable to determine version")
 }
 
+// GetReExecFromVersion returns the version if current execution binary is re-executed from
+// another version.
+func GetReExecFromVersion(ctx context.Context) string {
+	reExecFromVersion := os.Getenv(teleportToolsVersionReExecEnv)
+	if reExecFromVersion != "" {
+		if _, err := semver.NewVersion(reExecFromVersion); err != nil {
+			slog.WarnContext(ctx, "Failed to parse teleport 'TELEPORT_TOOLS_VERSION_REEXEC'", "error", err)
+			return ""
+		}
+	}
+	return reExecFromVersion
+}
+
 // packageURL defines URLs to the archive and their archive sha256 hash file, and marks
 // if this package is optional, for such case download needs to be ignored if package
 // not found in CDN.
diff --git a/tool/tsh/common/tsh.go b/tool/tsh/common/tsh.go
index 6c0e44ee427ee..5c56c68154fd3 100644
--- a/tool/tsh/common/tsh.go
+++ b/tool/tsh/common/tsh.go
@@ -1802,6 +1802,7 @@ func onVersion(cf *CLIConf) error {
 		proxyPublicAddr = ppa
 	}
 
+	reExecFromVersion := tools.GetReExecFromVersion(cf.Context)
 	format := strings.ToLower(cf.Format)
 	switch format {
 	case teleport.Text, "":
@@ -1810,8 +1811,11 @@ func onVersion(cf *CLIConf) error {
 			fmt.Printf("Proxy version: %s\n", proxyVersion)
 			fmt.Printf("Proxy: %s\n", proxyPublicAddr)
 		}
+		if reExecFromVersion != "" {
+			fmt.Printf("Re-executed from version: %s\n", reExecFromVersion)
+		}
 	case teleport.JSON, teleport.YAML:
-		out, err := serializeVersion(format, proxyVersion, proxyPublicAddr)
+		out, err := serializeVersion(format, proxyVersion, proxyPublicAddr, reExecFromVersion)
 		if err != nil {
 			return trace.Wrap(err)
 		}
@@ -1858,19 +1862,21 @@ type benchKubeOptions struct {
 	namespace string
 }
 
-func serializeVersion(format string, proxyVersion string, proxyPublicAddress string) (string, error) {
+func serializeVersion(format string, proxyVersion string, proxyPublicAddress string, reExecFromVersion string) (string, error) {
 	versionInfo := struct {
-		Version            string `json:"version"`
-		Gitref             string `json:"gitref"`
-		Runtime            string `json:"runtime"`
-		ProxyVersion       string `json:"proxyVersion,omitempty"`
-		ProxyPublicAddress string `json:"proxyPublicAddress,omitempty"`
+		Version               string `json:"version"`
+		Gitref                string `json:"gitref"`
+		Runtime               string `json:"runtime"`
+		ProxyVersion          string `json:"proxyVersion,omitempty"`
+		ProxyPublicAddress    string `json:"proxyPublicAddress,omitempty"`
+		ReExecutedFromVersion string `json:"reExecutedFromVersion,omitempty"`
 	}{
 		teleport.Version,
 		teleport.Gitref,
 		runtime.Version(),
 		proxyVersion,
 		proxyPublicAddress,
+		reExecFromVersion,
 	}
 	var out []byte
 	var err error
diff --git a/tool/tsh/common/tsh_test.go b/tool/tsh/common/tsh_test.go
index 873aacca28822..ba8c787527130 100644
--- a/tool/tsh/common/tsh_test.go
+++ b/tool/tsh/common/tsh_test.go
@@ -4164,6 +4164,7 @@ func TestSerializeVersion(t *testing.T) {
 
 		proxyVersion       string
 		proxyPublicAddress string
+		reExecFromVersion  string
 	}{
 		{
 			name: "no proxy version provided",
@@ -4180,12 +4181,21 @@ func TestSerializeVersion(t *testing.T) {
 				`{"version": %q, "gitref": %q, "runtime": %q, "proxyVersion": %q, "proxyPublicAddress": %q}`,
 				teleport.Version, teleport.Gitref, runtime.Version(), "1.33.7", "teleport.example.com:443"),
 		},
+		{
+			name:               "re-exec version provided",
+			proxyVersion:       "3.2.1",
+			proxyPublicAddress: "teleport.example.com:443",
+			reExecFromVersion:  "1.2.3",
+			expected: fmt.Sprintf(
+				`{"version": %q, "gitref": %q, "runtime": %q, "proxyVersion": %q, "reExecutedFromVersion": %q, "proxyPublicAddress": %q}`,
+				teleport.Version, teleport.Gitref, runtime.Version(), "3.2.1", "1.2.3", "teleport.example.com:443"),
+		},
 	}
 
 	for _, tC := range testCases {
 		t.Run(tC.name, func(t *testing.T) {
 			testSerialization(t, tC.expected, func(fmt string) (string, error) {
-				return serializeVersion(fmt, tC.proxyVersion, tC.proxyPublicAddress)
+				return serializeVersion(fmt, tC.proxyVersion, tC.proxyPublicAddress, tC.reExecFromVersion)
 			})
 		})
 	}