diff --git a/docs/pages/reference/signals.mdx b/docs/pages/reference/signals.mdx
index 95139796f935..31d30ce0795f 100644
--- a/docs/pages/reference/signals.mdx
+++ b/docs/pages/reference/signals.mdx
@@ -20,3 +20,4 @@ $ kill -SIG
 | `TERM`, `INT` | Immediate non-graceful shutdown. All existing connections will be closed after a very short delay. |
 | `USR2` | Forks a new Teleport daemon to serve new connections. |
 | `HUP` | Forks a new Teleport daemon to serve new connections **and** initiates the graceful shutdown of the existing process, same as `SIGQUIT`. |
+| `CONT` | Re-open the log file (useful for `logrotate`). |
diff --git a/lib/config/configuration.go b/lib/config/configuration.go
index 589113a4476c..7eb46a90fd83 100644
--- a/lib/config/configuration.go
+++ b/lib/config/configuration.go
@@ -26,6 +26,7 @@ import (
 	"crypto/x509"
 	"errors"
 	"io"
+	"io/fs"
 	"log/slog"
 	"maps"
 	"net"
@@ -756,12 +757,12 @@ func applyLogConfig(loggerConfig Log, cfg *servicecfg.Config) error {
 	var w io.Writer
 	switch loggerConfig.Output {
 	case "":
-		w = os.Stderr
+		w = logutils.NewSharedWriter(os.Stderr)
 	case "stderr", "error", "2":
-		w = os.Stderr
+		w = logutils.NewSharedWriter(os.Stderr)
 		cfg.Console = io.Discard // disable console printing
 	case "stdout", "out", "1":
-		w = os.Stdout
+		w = logutils.NewSharedWriter(os.Stdout)
 		cfg.Console = io.Discard // disable console printing
 	case teleport.Syslog:
 		w = os.Stderr
@@ -779,14 +780,22 @@ func applyLogConfig(loggerConfig Log, cfg *servicecfg.Config) error {
 
 		logger.ReplaceHooks(make(log.LevelHooks))
 		logger.AddHook(hook)
+		// If syslog output has been configured and is supported by the operating system,
+		// then the shared writer is not needed because the syslog writer is already
+		// protected with a mutex.
 		w = sw
 	default:
 		// assume it's a file path:
-		logFile, err := os.Create(loggerConfig.Output)
+		var flag int = os.O_WRONLY | os.O_CREATE | os.O_APPEND
+		var mode = fs.FileMode(0666)
+		logFile, err := os.OpenFile(loggerConfig.Output, flag, mode)
 		if err != nil {
 			return trace.Wrap(err, "failed to create the log file")
 		}
-		w = logFile
+		fileWriter := logutils.NewFileSharedWriter(logFile, flag, mode)
+		cfg.LogFileReopen = fileWriter.Reopen
+
+		w = fileWriter
 	}
 
 	level := new(slog.LevelVar)
@@ -815,12 +824,6 @@ func applyLogConfig(loggerConfig Log, cfg *servicecfg.Config) error {
 		return trace.Wrap(err)
 	}
 
-	// If syslog output has been configured and is supported by the operating system,
-	// then the shared writer is not needed because the syslog writer is already
-	// protected with a mutex.
-	if len(logger.Hooks) == 0 {
-		w = logutils.NewSharedWriter(w)
-	}
 	var slogLogger *slog.Logger
 	switch strings.ToLower(loggerConfig.Format.Output) {
 	case "":
diff --git a/lib/service/servicecfg/config.go b/lib/service/servicecfg/config.go
index 456321cdf35e..7d547d60df51 100644
--- a/lib/service/servicecfg/config.go
+++ b/lib/service/servicecfg/config.go
@@ -227,6 +227,9 @@ type Config struct {
 	Logger *slog.Logger
 	// LoggerLevel defines the Logger log level.
 	LoggerLevel *slog.LevelVar
+	// LogFileReopen is used to close and re-open the log file.
+	// If the logger is not writting to a log file, this is a no-op.
+	LogFileReopen func() error
 
 	// PluginRegistry allows adding enterprise logic to Teleport services
 	PluginRegistry plugin.Registry
@@ -592,6 +595,8 @@ func ApplyDefaults(cfg *Config) {
 	cfg.MaxRetryPeriod = defaults.MaxWatcherBackoff
 	cfg.Testing.ConnectFailureC = make(chan time.Duration, 1)
 	cfg.CircuitBreakerConfig = breaker.DefaultBreakerConfig(cfg.Clock)
+
+	cfg.LogFileReopen = func() error { return nil }
 }
 
 // FileDescriptor is a file descriptor associated
diff --git a/lib/service/signals.go b/lib/service/signals.go
index ebcdadfac501..3eb8af9a580e 100644
--- a/lib/service/signals.go
+++ b/lib/service/signals.go
@@ -76,6 +76,7 @@ var teleportSignals = []os.Signal{
 	syscall.SIGUSR1, // log process diagnostic info
 	syscall.SIGUSR2, // initiate process restart procedure
 	syscall.SIGHUP,  // graceful restart procedure
+	syscall.SIGCONT, // Re-open the log file
 }
 
 // WaitForSignals waits for system signals and processes them.
@@ -151,6 +152,11 @@ func (process *TeleportProcess) WaitForSignals(ctx context.Context, sigC <-chan
 				process.Shutdown(timeoutCtx)
 				process.logger.InfoContext(process.ExitContext(), "All services stopped, exiting.")
 				return nil
+			case syscall.SIGCONT:
+				process.logger.InfoContext(process.ExitContext(), "Rotating log file.")
+				if err := process.Config.LogFileReopen(); err != nil {
+					return trace.Wrap(err)
+				}
 			default:
 				process.logger.InfoContext(process.ExitContext(), "Ignoring unknown signal.", "signal", signal)
 			}
diff --git a/lib/utils/log/writer.go b/lib/utils/log/writer.go
index 77cf3037a8b6..510b954be946 100644
--- a/lib/utils/log/writer.go
+++ b/lib/utils/log/writer.go
@@ -20,7 +20,11 @@ package log
 
 import (
 	"io"
+	"io/fs"
+	"os"
 	"sync"
+
+	"github.com/gravitational/trace"
 )
 
 // SharedWriter is an [io.Writer] implementation that protects
@@ -43,3 +47,39 @@ func (s *SharedWriter) Write(p []byte) (int, error) {
 func NewSharedWriter(w io.Writer) *SharedWriter {
 	return &SharedWriter{Writer: w}
 }
+
+// FileSharedWriter is similar to SharedWriter except that it requires a os.File instead of a io.Writer.
+// This is to allow the File reopen required by logrotate and similar tools.
+// SharedWriter must be used for log destinations that don't have the reopen requirement, like stdout and stderr.
+// This is thread safe.
+type FileSharedWriter struct {
+	*os.File
+	fileFlag int
+	fileMode fs.FileMode
+	mu       sync.Mutex
+}
+
+func (s *FileSharedWriter) Write(p []byte) (int, error) {
+	s.mu.Lock()
+	defer s.mu.Unlock()
+
+	return s.File.Write(p)
+}
+
+// Reopen closes the file and opens it again using APPEND mode.
+func (s *FileSharedWriter) Reopen() (err error) {
+	s.mu.Lock()
+	defer s.mu.Unlock()
+
+	if err := s.Close(); err != nil {
+		return trace.Wrap(err)
+	}
+
+	s.File, err = os.OpenFile(s.Name(), s.fileFlag, s.fileMode)
+	return trace.Wrap(err)
+}
+
+// NewFileSharedWriter wraps the provided [os.File] in a writer that is thread safe.
+func NewFileSharedWriter(f *os.File, flag int, mode fs.FileMode) *FileSharedWriter {
+	return &FileSharedWriter{File: f, fileFlag: flag, fileMode: mode}
+}