diff --git a/client/internal/engine.go b/client/internal/engine.go
index 452075da8..d6d125582 100644
--- a/client/internal/engine.go
+++ b/client/internal/engine.go
@@ -82,6 +82,12 @@ const (
 	PeerConnectionTimeoutMax = 45000 // ms
 	PeerConnectionTimeoutMin = 30000 // ms
 	disableAutoUpdate        = "disabled"
+
+	// systemInfoTimeout bounds how long the sync loop waits for system info / posture
+	// check gathering. The gathering runs uncancellable system calls (process scan,
+	// exec, os.Stat); without this bound a single stuck call freezes handleSync, and
+	// thus syncMsgMux, for as long as the call hangs (observed multi-minute freezes).
+	systemInfoTimeout = 15 * time.Second
 )
 
 var ErrResetConnection = fmt.Errorf("reset connection")
@@ -1066,11 +1072,23 @@ func (e *Engine) updateChecksIfNew(checks []*mgmProto.Checks) error {
 	}
 	e.checks = checks
 
-	info, err := system.GetInfoWithChecks(e.ctx, checks)
-	if err != nil {
-		log.Warnf("failed to get system info with checks: %v", err)
-		info = system.GetInfo(e.ctx)
+	info, ok := system.GetInfoWithChecksTimeout(e.ctx, systemInfoTimeout, checks)
+	if !ok {
+		// Gathering timed out; skip the meta sync this cycle rather than blocking the
+		// sync loop (and syncMsgMux) on a stuck system call. A later sync will retry.
+		return nil
 	}
+	e.applyInfoFlags(info)
+
+	if err := e.mgmClient.SyncMeta(info); err != nil {
+		log.Errorf("could not sync meta: error %s", err)
+		return err
+	}
+	return nil
+}
+
+// applyInfoFlags sets the engine's config-derived feature flags on the gathered system info.
+func (e *Engine) applyInfoFlags(info *system.Info) {
 	info.SetFlags(
 		e.config.RosenpassEnabled,
 		e.config.RosenpassPermissive,
@@ -1089,12 +1107,6 @@ func (e *Engine) updateChecksIfNew(checks []*mgmProto.Checks) error {
 		e.config.EnableSSHRemotePortForwarding,
 		e.config.DisableSSHAuth,
 	)
-
-	if err := e.mgmClient.SyncMeta(info); err != nil {
-		log.Errorf("could not sync meta: error %s", err)
-		return err
-	}
-	return nil
 }
 
 func (e *Engine) updateConfig(conf *mgmProto.PeerConfig) error {
@@ -1240,31 +1252,15 @@ func (e *Engine) receiveManagementEvents() {
 	e.shutdownWg.Add(1)
 	go func() {
 		defer e.shutdownWg.Done()
-		info, err := system.GetInfoWithChecks(e.ctx, e.checks)
-		if err != nil {
-			log.Warnf("failed to get system info with checks: %v", err)
+		info, ok := system.GetInfoWithChecksTimeout(e.ctx, systemInfoTimeout, e.checks)
+		if !ok {
+			// Gathering timed out; connect the stream with base info so management
+			// connectivity still comes up rather than blocking here.
 			info = system.GetInfo(e.ctx)
 		}
-		info.SetFlags(
-			e.config.RosenpassEnabled,
-			e.config.RosenpassPermissive,
-			&e.config.ServerSSHAllowed,
-			e.config.DisableClientRoutes,
-			e.config.DisableServerRoutes,
-			e.config.DisableDNS,
-			e.config.DisableFirewall,
-			e.config.BlockLANAccess,
-			e.config.BlockInbound,
-			e.config.DisableIPv6,
-			e.config.LazyConnectionEnabled,
-			e.config.EnableSSHRoot,
-			e.config.EnableSSHSFTP,
-			e.config.EnableSSHLocalPortForwarding,
-			e.config.EnableSSHRemotePortForwarding,
-			e.config.DisableSSHAuth,
-		)
+		e.applyInfoFlags(info)
 
-		err = e.mgmClient.Sync(e.ctx, info, e.handleSync)
+		err := e.mgmClient.Sync(e.ctx, info, e.handleSync)
 		if err != nil {
 			// happens if management is unavailable for a long time.
 			// We want to cancel the operation of the whole client
diff --git a/client/system/info.go b/client/system/info.go
index 477d5162b..3f4a0aab7 100644
--- a/client/system/info.go
+++ b/client/system/info.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"net/netip"
 	"strings"
+	"time"
 
 	log "github.com/sirupsen/logrus"
 	"google.golang.org/grpc/metadata"
@@ -166,3 +167,34 @@ func GetInfoWithChecks(ctx context.Context, checks []*proto.Checks) (*Info, erro
 	log.Debugf("all system information gathered successfully")
 	return info, nil
 }
+
+// GetInfoWithChecksTimeout is GetInfoWithChecks bounded by timeout. Posture-check gathering
+// runs uncancellable system calls (process enumeration, os.Stat), so calling it inline can
+// block the caller for as long as such a call hangs. It runs in a goroutine instead: if it
+// does not return within timeout the caller gets (nil, false) and should proceed with
+// degraded behavior rather than block. On a gathering error it falls back to base GetInfo.
+//
+// The buffered channel lets the abandoned goroutine finish and exit once its blocking call
+// returns, so it does not leak beyond the duration of that call.
+func GetInfoWithChecksTimeout(ctx context.Context, timeout time.Duration, checks []*proto.Checks) (*Info, bool) {
+	ctx, cancel := context.WithTimeout(ctx, timeout)
+	defer cancel()
+
+	infoCh := make(chan *Info, 1)
+	go func() {
+		info, err := GetInfoWithChecks(ctx, checks)
+		if err != nil {
+			log.Warnf("failed to get system info with checks: %v", err)
+			info = GetInfo(ctx)
+		}
+		infoCh <- info
+	}()
+
+	select {
+	case info := <-infoCh:
+		return info, true
+	case <-ctx.Done():
+		log.Warnf("gathering system info with checks timed out after %s", timeout)
+		return nil, false
+	}
+}