diff --git a/internal/server/middleware/deprecation.go b/internal/server/middleware/deprecation.go
new file mode 100644
index 0000000..cd30eaa
--- /dev/null
+++ b/internal/server/middleware/deprecation.go
@@ -0,0 +1,16 @@
+package middleware
+
+import (
+	"github.com/labstack/echo/v5"
+)
+
+// DeprecationMiddleware adds deprecation warning to responses
+// for old endpoints that are being phased out in favor of /api/v1/*
+func DeprecationMiddleware(next echo.HandlerFunc) echo.HandlerFunc {
+	return func(c *echo.Context) error {
+		// Add deprecation warning header
+		c.Response().Header().Add("Warning", `299 - "Deprecated: This endpoint is deprecated. Use /api/v1/ endpoints instead."`)
+		c.Response().Header().Add("Deprecation", "true")
+		return next(c)
+	}
+}
diff --git a/internal/server/routes.go b/internal/server/routes.go
index bc33c17..ec8057e 100644
--- a/internal/server/routes.go
+++ b/internal/server/routes.go
@@ -58,47 +58,52 @@ func (s *Server) RegisterRoutes() http.Handler {
 	// Swagger UI
 	e.GET("/swagger/*", echoSwagger.WrapHandler)
 
+	// ============================================
+	// Legacy Endpoints (Deprecated - use /api/v1/ instead)
+	// ============================================
+	deprecatedMiddleware := middleware.DeprecationMiddleware
+
 	index := NewIndexHandler()
-	e.GET("/version", index.GetVersion)
-	e.GET("/dbtest", index.GetDBTest)
-	e.GET("/health", index.HealthCheck)
-	e.GET("/character", index.GetCharacter)
-	e.GET("/characters", index.GetCharacterList)
+	e.GET("/version", deprecatedMiddleware(index.GetVersion))
+	e.GET("/dbtest", deprecatedMiddleware(index.GetDBTest))
+	e.GET("/health", deprecatedMiddleware(index.HealthCheck))
+	e.GET("/character", deprecatedMiddleware(index.GetCharacter))
+	e.GET("/characters", deprecatedMiddleware(index.GetCharacterList))
 
 	download := NewDownloadHandler()
-	e.GET("/download", download.checkLatest)
-	e.GET("/download/list", download.listAssetsOfLatest)
-	e.GET("/download/windows", download.downloadLatestWindows)
-	e.GET("/download/linux", download.downloadLatestLinux)
+	e.GET("/download", deprecatedMiddleware(download.checkLatest))
+	e.GET("/download/list", deprecatedMiddleware(download.listAssetsOfLatest))
+	e.GET("/download/windows", deprecatedMiddleware(download.downloadLatestWindows))
+	e.GET("/download/linux", deprecatedMiddleware(download.downloadLatestLinux))
 
 	sync := NewSyncHandler()
 	syncGroup := e.Group("/sync")
-	syncGroup.GET("", sync.SyncGamesNewOnlyChanges)
-	syncGroup.GET("/progress", sync.SyncProgress)
-	syncGroup.GET("/new", sync.SyncGamesNewOnlyChanges)
-	syncGroup.GET("/full", sync.SyncGamesNewFull)
-	syncGroup.GET("/new/full", sync.SyncGamesNewFull)
-	syncGroup.GET("/quick", sync.SyncGamesNewOnlyChanges)
-	syncGroup.GET("/reset", sync.ResetGames)
+	syncGroup.GET("", deprecatedMiddleware(sync.SyncGamesNewOnlyChanges))
+	syncGroup.GET("/progress", deprecatedMiddleware(sync.SyncProgress))
+	syncGroup.GET("/new", deprecatedMiddleware(sync.SyncGamesNewOnlyChanges))
+	syncGroup.GET("/full", deprecatedMiddleware(sync.SyncGamesNewFull))
+	syncGroup.GET("/new/full", deprecatedMiddleware(sync.SyncGamesNewFull))
+	syncGroup.GET("/quick", deprecatedMiddleware(sync.SyncGamesNewOnlyChanges))
+	syncGroup.GET("/reset", deprecatedMiddleware(sync.ResetGames))
 
 	music := NewMusicHandler()
 	musicGroup := e.Group("/music")
-	musicGroup.GET("", music.GetSong)
-	musicGroup.GET("/soundTest", music.GetSoundCheckSong)
-	musicGroup.GET("/reset", music.ResetMusic)
-	musicGroup.GET("/rand", music.GetRandomSong)
-	musicGroup.GET("/rand/low", music.GetRandomSongLowChance)
-	musicGroup.GET("/rand/classic", music.GetRandomSongClassic)
-	musicGroup.GET("/info", music.GetSongInfo)
-	musicGroup.GET("/list", music.GetPlayedSongs)
-	musicGroup.GET("/next", music.GetNextSong)
-	musicGroup.GET("/previous", music.GetPreviousSong)
-	musicGroup.GET("/all", music.GetAllGamesRandom)
-	musicGroup.GET("/all/order", music.GetAllGames)
-	musicGroup.GET("/all/random", music.GetAllGamesRandom)
-	musicGroup.PUT("/played", music.PutPlayed)
-	musicGroup.GET("/addQue", music.AddLatestToQue)
-	musicGroup.GET("/addPlayed", music.AddLatestPlayed)
+	musicGroup.GET("", deprecatedMiddleware(music.GetSong))
+	musicGroup.GET("/soundTest", deprecatedMiddleware(music.GetSoundCheckSong))
+	musicGroup.GET("/reset", deprecatedMiddleware(music.ResetMusic))
+	musicGroup.GET("/rand", deprecatedMiddleware(music.GetRandomSong))
+	musicGroup.GET("/rand/low", deprecatedMiddleware(music.GetRandomSongLowChance))
+	musicGroup.GET("/rand/classic", deprecatedMiddleware(music.GetRandomSongClassic))
+	musicGroup.GET("/info", deprecatedMiddleware(music.GetSongInfo))
+	musicGroup.GET("/list", deprecatedMiddleware(music.GetPlayedSongs))
+	musicGroup.GET("/next", deprecatedMiddleware(music.GetNextSong))
+	musicGroup.GET("/previous", deprecatedMiddleware(music.GetPreviousSong))
+	musicGroup.GET("/all", deprecatedMiddleware(music.GetAllGamesRandom))
+	musicGroup.GET("/all/order", deprecatedMiddleware(music.GetAllGames))
+	musicGroup.GET("/all/random", deprecatedMiddleware(music.GetAllGamesRandom))
+	musicGroup.PUT("/played", deprecatedMiddleware(music.PutPlayed))
+	musicGroup.GET("/addQue", deprecatedMiddleware(music.AddLatestToQue))
+	musicGroup.GET("/addPlayed", deprecatedMiddleware(music.AddLatestPlayed))
 
 	// ============================================
 	// API v1 Routes with Token Authentication