diff --git a/core/playlists.go b/core/playlists.go
index f98179f88..ed90cc23b 100644
--- a/core/playlists.go
+++ b/core/playlists.go
@@ -1,6 +1,7 @@
 package core
 
 import (
+	"cmp"
 	"context"
 	"encoding/json"
 	"errors"
@@ -9,7 +10,7 @@ import (
 	"net/url"
 	"os"
 	"path/filepath"
-	"regexp"
+	"slices"
 	"strings"
 	"time"
 
@@ -194,22 +195,35 @@ func (s *playlists) parseM3U(ctx context.Context, pls *model.Playlist, folder *m
 			}
 			filteredLines = append(filteredLines, line)
 		}
-		paths, err := s.normalizePaths(ctx, pls, folder, filteredLines)
+		resolvedPaths, err := s.resolvePaths(ctx, folder, filteredLines)
 		if err != nil {
-			log.Warn(ctx, "Error normalizing paths in playlist", "playlist", pls.Name, err)
+			log.Warn(ctx, "Error resolving paths in playlist", "playlist", pls.Name, err)
 			continue
 		}
-		found, err := mediaFileRepository.FindByPaths(paths)
+
+		// Normalize to NFD for filesystem compatibility (macOS). Database stores paths in NFD.
+		// See https://github.com/navidrome/navidrome/issues/4663
+		resolvedPaths = slice.Map(resolvedPaths, func(path string) string {
+			return strings.ToLower(norm.NFD.String(path))
+		})
+
+		found, err := mediaFileRepository.FindByPaths(resolvedPaths)
 		if err != nil {
 			log.Warn(ctx, "Error reading files from DB", "playlist", pls.Name, err)
 			continue
 		}
+		// Build lookup map with library-qualified keys, normalized for comparison
 		existing := make(map[string]int, len(found))
 		for idx := range found {
-			existing[normalizePathForComparison(found[idx].Path)] = idx
+			// Normalize to lowercase for case-insensitive comparison
+			// Key format: "libraryID:path"
+			key := fmt.Sprintf("%d:%s", found[idx].LibraryID, strings.ToLower(found[idx].Path))
+			existing[key] = idx
 		}
-		for _, path := range paths {
-			idx, ok := existing[normalizePathForComparison(path)]
+
+		// Find media files in the order of the resolved paths, to keep playlist order
+		for _, path := range resolvedPaths {
+			idx, ok := existing[path]
 			if ok {
 				mfs = append(mfs, found[idx])
 			} else {
@@ -226,69 +240,150 @@ func (s *playlists) parseM3U(ctx context.Context, pls *model.Playlist, folder *m
 	return nil
 }
 
-// normalizePathForComparison normalizes a file path to NFC form and converts to lowercase
-// for consistent comparison. This fixes Unicode normalization issues on macOS where
-// Apple Music creates playlists with NFC-encoded paths but the filesystem uses NFD.
-func normalizePathForComparison(path string) string {
-	return strings.ToLower(norm.NFC.String(path))
+// pathResolution holds the result of resolving a playlist path to a library-relative path.
+type pathResolution struct {
+	absolutePath string
+	libraryPath  string
+	libraryID    int
+	valid        bool
 }
 
-// TODO This won't work for multiple libraries
-func (s *playlists) normalizePaths(ctx context.Context, pls *model.Playlist, folder *model.Folder, lines []string) ([]string, error) {
-	libRegex, err := s.compileLibraryPaths(ctx)
+// ToQualifiedString converts the path resolution to a library-qualified string with forward slashes.
+// Format: "libraryID:relativePath" with forward slashes for path separators.
+func (r pathResolution) ToQualifiedString() (string, error) {
+	if !r.valid {
+		return "", fmt.Errorf("invalid path resolution")
+	}
+	relativePath, err := filepath.Rel(r.libraryPath, r.absolutePath)
 	if err != nil {
-		return nil, err
+		return "", err
 	}
-
-	res := make([]string, 0, len(lines))
-	for idx, line := range lines {
-		var libPath string
-		var filePath string
-
-		if folder != nil && !filepath.IsAbs(line) {
-			libPath = folder.LibraryPath
-			filePath = filepath.Join(folder.AbsolutePath(), line)
-		} else {
-			cleanLine := filepath.Clean(line)
-			if libPath = libRegex.FindString(cleanLine); libPath != "" {
-				filePath = cleanLine
-			}
-		}
-
-		if libPath != "" {
-			if rel, err := filepath.Rel(libPath, filePath); err == nil {
-				res = append(res, rel)
-			} else {
-				log.Debug(ctx, "Error getting relative path", "playlist", pls.Name, "path", line, "libPath", libPath,
-					"filePath", filePath, err)
-			}
-		} else {
-			log.Warn(ctx, "Path in playlist not found in any library", "path", line, "line", idx)
-		}
-	}
-	return slice.Map(res, filepath.ToSlash), nil
+	// Convert path separators to forward slashes
+	return fmt.Sprintf("%d:%s", r.libraryID, filepath.ToSlash(relativePath)), nil
 }
 
-func (s *playlists) compileLibraryPaths(ctx context.Context) (*regexp.Regexp, error) {
-	libs, err := s.ds.Library(ctx).GetAll()
-	if err != nil {
-		return nil, err
-	}
+// libraryMatcher holds sorted libraries with cleaned paths for efficient path matching.
+type libraryMatcher struct {
+	libraries    model.Libraries
+	cleanedPaths []string
+}
 
-	// Create regex patterns for each library path
-	patterns := make([]string, len(libs))
+// findLibraryForPath finds which library contains the given absolute path.
+// Returns library ID and path, or 0 and empty string if not found.
+func (lm *libraryMatcher) findLibraryForPath(absolutePath string) (int, string) {
+	// Check sorted libraries (longest path first) to find the best match
+	for i, cleanLibPath := range lm.cleanedPaths {
+		// Check if absolutePath is under this library path
+		if strings.HasPrefix(absolutePath, cleanLibPath) {
+			// Ensure it's a proper path boundary (not just a prefix)
+			if len(absolutePath) == len(cleanLibPath) || absolutePath[len(cleanLibPath)] == filepath.Separator {
+				return lm.libraries[i].ID, cleanLibPath
+			}
+		}
+	}
+	return 0, ""
+}
+
+// newLibraryMatcher creates a libraryMatcher with libraries sorted by path length (longest first).
+// This ensures correct matching when library paths are prefixes of each other.
+// Example: /music-classical must be checked before /music
+// Otherwise, /music-classical/track.mp3 would match /music instead of /music-classical
+func newLibraryMatcher(libs model.Libraries) *libraryMatcher {
+	// Sort libraries by path length (descending) to ensure longest paths match first.
+	slices.SortFunc(libs, func(i, j model.Library) int {
+		return cmp.Compare(len(j.Path), len(i.Path)) // Reverse order for descending
+	})
+
+	// Pre-clean all library paths once for efficient matching
+	cleanedPaths := make([]string, len(libs))
 	for i, lib := range libs {
-		cleanPath := filepath.Clean(lib.Path)
-		escapedPath := regexp.QuoteMeta(cleanPath)
-		patterns[i] = fmt.Sprintf("^%s(?:/|$)", escapedPath)
+		cleanedPaths[i] = filepath.Clean(lib.Path)
 	}
-	// Combine all patterns into a single regex
-	combinedPattern := strings.Join(patterns, "|")
-	re, err := regexp.Compile(combinedPattern)
+	return &libraryMatcher{
+		libraries:    libs,
+		cleanedPaths: cleanedPaths,
+	}
+}
+
+// pathResolver handles path resolution logic for playlist imports.
+type pathResolver struct {
+	matcher *libraryMatcher
+}
+
+// newPathResolver creates a pathResolver with libraries loaded from the datastore.
+func newPathResolver(ctx context.Context, ds model.DataStore) (*pathResolver, error) {
+	libs, err := ds.Library(ctx).GetAll()
 	if err != nil {
-		return nil, fmt.Errorf("compiling library paths `%s`: %w", combinedPattern, err)
+		return nil, err
 	}
-	return re, nil
+	matcher := newLibraryMatcher(libs)
+	return &pathResolver{matcher: matcher}, nil
+}
+
+// resolvePath determines the absolute path and library path for a playlist entry.
+// For absolute paths, it uses them directly.
+// For relative paths, it resolves them relative to the playlist's folder location.
+// Example: playlist at /music/playlists/test.m3u with line "../songs/abc.mp3"
+//
+//	resolves to /music/songs/abc.mp3
+func (r *pathResolver) resolvePath(line string, folder *model.Folder) pathResolution {
+	var absolutePath string
+	if folder != nil && !filepath.IsAbs(line) {
+		// Resolve relative path to absolute path based on playlist location
+		absolutePath = filepath.Clean(filepath.Join(folder.AbsolutePath(), line))
+	} else {
+		// Use absolute path directly after cleaning
+		absolutePath = filepath.Clean(line)
+	}
+
+	return r.findInLibraries(absolutePath)
+}
+
+// findInLibraries matches an absolute path against all known libraries and returns
+// a pathResolution with the library information. Returns an invalid resolution if
+// the path is not found in any library.
+func (r *pathResolver) findInLibraries(absolutePath string) pathResolution {
+	libID, libPath := r.matcher.findLibraryForPath(absolutePath)
+	if libID == 0 {
+		return pathResolution{valid: false}
+	}
+	return pathResolution{
+		absolutePath: absolutePath,
+		libraryPath:  libPath,
+		libraryID:    libID,
+		valid:        true,
+	}
+}
+
+// resolvePaths converts playlist file paths to library-qualified paths (format: "libraryID:relativePath").
+// For relative paths, it resolves them to absolute paths first, then determines which
+// library they belong to. This allows playlists to reference files across library boundaries.
+func (s *playlists) resolvePaths(ctx context.Context, folder *model.Folder, lines []string) ([]string, error) {
+	resolver, err := newPathResolver(ctx, s.ds)
+	if err != nil {
+		return nil, err
+	}
+
+	results := make([]string, 0, len(lines))
+	for idx, line := range lines {
+		resolution := resolver.resolvePath(line, folder)
+
+		if !resolution.valid {
+			log.Warn(ctx, "Path in playlist not found in any library", "path", line, "line", idx)
+			continue
+		}
+
+		qualifiedPath, err := resolution.ToQualifiedString()
+		if err != nil {
+			log.Debug(ctx, "Error getting library-qualified path", "path", line,
+				"libPath", resolution.libraryPath, "filePath", resolution.absolutePath, err)
+			continue
+		}
+
+		results = append(results, qualifiedPath)
+	}
+
+	return results, nil
 }
 
 func (s *playlists) updatePlaylist(ctx context.Context, newPls *model.Playlist) error {
diff --git a/core/playlists_internal_test.go b/core/playlists_internal_test.go
new file mode 100644
index 000000000..88e36cc3a
--- /dev/null
+++ b/core/playlists_internal_test.go
@@ -0,0 +1,406 @@
+package core
+
+import (
+	"context"
+
+	"github.com/navidrome/navidrome/model"
+	"github.com/navidrome/navidrome/tests"
+	. "github.com/onsi/ginkgo/v2"
+	. "github.com/onsi/gomega"
+)
+
+var _ = Describe("libraryMatcher", func() {
+	var ds *tests.MockDataStore
+	var mockLibRepo *tests.MockLibraryRepo
+	ctx := context.Background()
+
+	BeforeEach(func() {
+		mockLibRepo = &tests.MockLibraryRepo{}
+		ds = &tests.MockDataStore{
+			MockedLibrary: mockLibRepo,
+		}
+	})
+
+	// Helper function to create a libraryMatcher from the mock datastore
+	createMatcher := func(ds model.DataStore) *libraryMatcher {
+		libs, err := ds.Library(ctx).GetAll()
+		Expect(err).ToNot(HaveOccurred())
+		return newLibraryMatcher(libs)
+	}
+
+	Describe("Longest library path matching", func() {
+		It("matches the longest library path when multiple libraries share a prefix", func() {
+			// Setup libraries with prefix conflicts
+			mockLibRepo.SetData([]model.Library{
+				{ID: 1, Path: "/music"},
+				{ID: 2, Path: "/music-classical"},
+				{ID: 3, Path: "/music-classical/opera"},
+			})
+
+			matcher := createMatcher(ds)
+
+			// Test that longest path matches first and returns correct library ID
+			testCases := []struct {
+				path            string
+				expectedLibID   int
+				expectedLibPath string
+			}{
+				{"/music-classical/opera/track.mp3", 3, "/music-classical/opera"},
+				{"/music-classical/track.mp3", 2, "/music-classical"},
+				{"/music/track.mp3", 1, "/music"},
+				{"/music-classical/opera/subdir/file.mp3", 3, "/music-classical/opera"},
+			}
+
+			for _, tc := range testCases {
+				libID, libPath := matcher.findLibraryForPath(tc.path)
+				Expect(libID).To(Equal(tc.expectedLibID), "Path %s should match library ID %d, but got %d", tc.path, tc.expectedLibID, libID)
+				Expect(libPath).To(Equal(tc.expectedLibPath), "Path %s should match library path %s, but got %s", tc.path, tc.expectedLibPath, libPath)
+			}
+		})
+
+		It("handles libraries with similar prefixes but different structures", func() {
+			mockLibRepo.SetData([]model.Library{
+				{ID: 1, Path: "/home/user/music"},
+				{ID: 2, Path: "/home/user/music-backup"},
+			})
+
+			matcher := createMatcher(ds)
+
+			// Test that music-backup library is matched correctly
+			libID, libPath := matcher.findLibraryForPath("/home/user/music-backup/track.mp3")
+			Expect(libID).To(Equal(2))
+			Expect(libPath).To(Equal("/home/user/music-backup"))
+
+			// Test that music library is still matched correctly
+			libID, libPath = matcher.findLibraryForPath("/home/user/music/track.mp3")
+			Expect(libID).To(Equal(1))
+			Expect(libPath).To(Equal("/home/user/music"))
+		})
+
+		It("matches path that is exactly the library root", func() {
+			mockLibRepo.SetData([]model.Library{
+				{ID: 1, Path: "/music"},
+				{ID: 2, Path: "/music-classical"},
+			})
+
+			matcher := createMatcher(ds)
+
+			// Exact library path should match
+			libID, libPath := matcher.findLibraryForPath("/music-classical")
+			Expect(libID).To(Equal(2))
+			Expect(libPath).To(Equal("/music-classical"))
+		})
+
+		It("handles complex nested library structures", func() {
+			mockLibRepo.SetData([]model.Library{
+				{ID: 1, Path: "/media"},
+				{ID: 2, Path: "/media/audio"},
+				{ID: 3, Path: "/media/audio/classical"},
+				{ID: 4, Path: "/media/audio/classical/baroque"},
+			})
+
+			matcher := createMatcher(ds)
+
+			testCases := []struct {
+				path            string
+				expectedLibID   int
+				expectedLibPath string
+			}{
+				{"/media/audio/classical/baroque/bach/track.mp3", 4, "/media/audio/classical/baroque"},
+				{"/media/audio/classical/mozart/track.mp3", 3, "/media/audio/classical"},
+				{"/media/audio/rock/track.mp3", 2, "/media/audio"},
+				{"/media/video/movie.mp4", 1, "/media"},
+			}
+
+			for _, tc := range testCases {
+				libID, libPath := matcher.findLibraryForPath(tc.path)
+				Expect(libID).To(Equal(tc.expectedLibID), "Path %s should match library ID %d", tc.path, tc.expectedLibID)
+				Expect(libPath).To(Equal(tc.expectedLibPath), "Path %s should match library path %s", tc.path, tc.expectedLibPath)
+			}
+		})
+	})
+
+	Describe("Edge cases", func() {
+		It("handles empty library list", func() {
+			mockLibRepo.SetData([]model.Library{})
+
+			matcher := createMatcher(ds)
+			Expect(matcher).ToNot(BeNil())
+
+			// Should not match anything
+			libID, libPath := matcher.findLibraryForPath("/music/track.mp3")
+			Expect(libID).To(Equal(0))
+			Expect(libPath).To(BeEmpty())
+		})
+
+		It("handles single library", func() {
+			mockLibRepo.SetData([]model.Library{
+				{ID: 1, Path: "/music"},
+			})
+
+			matcher := createMatcher(ds)
+
+			libID, libPath := matcher.findLibraryForPath("/music/track.mp3")
+			Expect(libID).To(Equal(1))
+			Expect(libPath).To(Equal("/music"))
+		})
+
+		It("handles libraries with special characters in paths", func() {
+			mockLibRepo.SetData([]model.Library{
+				{ID: 1, Path: "/music[test]"},
+				{ID: 2, Path: "/music(backup)"},
+			})
+
+			matcher := createMatcher(ds)
+			Expect(matcher).ToNot(BeNil())
+
+			// Special characters should match literally
+			libID, libPath := matcher.findLibraryForPath("/music[test]/track.mp3")
+			Expect(libID).To(Equal(1))
+			Expect(libPath).To(Equal("/music[test]"))
+		})
+	})
+
+	Describe("Path matching order", func() {
+		It("ensures longest paths match first", func() {
+			mockLibRepo.SetData([]model.Library{
+				{ID: 1, Path: "/a"},
+				{ID: 2, Path: "/ab"},
+				{ID: 3, Path: "/abc"},
+			})
+
+			matcher := createMatcher(ds)
+
+			// Verify that longer paths match correctly (not cut off by shorter prefix)
+			testCases := []struct {
+				path          string
+				expectedLibID int
+			}{
+				{"/abc/file.mp3", 3},
+				{"/ab/file.mp3", 2},
+				{"/a/file.mp3", 1},
+			}
+
+			for _, tc := range testCases {
+				libID, _ := matcher.findLibraryForPath(tc.path)
+				Expect(libID).To(Equal(tc.expectedLibID), "Path %s should match library ID %d", tc.path, tc.expectedLibID)
+			}
+		})
+	})
+})
+
+var _ = Describe("pathResolver", func() {
+	var ds *tests.MockDataStore
+	var mockLibRepo *tests.MockLibraryRepo
+	var resolver *pathResolver
+	ctx := context.Background()
+
+	BeforeEach(func() {
+		mockLibRepo = &tests.MockLibraryRepo{}
+		ds = &tests.MockDataStore{
+			MockedLibrary: mockLibRepo,
+		}
+
+		// Setup test libraries
+		mockLibRepo.SetData([]model.Library{
+			{ID: 1, Path: "/music"},
+			{ID: 2, Path: "/music-classical"},
+			{ID: 3, Path: "/podcasts"},
+		})
+
+		var err error
+		resolver, err = newPathResolver(ctx, ds)
+		Expect(err).ToNot(HaveOccurred())
+	})
+
+	Describe("resolvePath", func() {
+		It("resolves absolute paths", func() {
+			resolution := resolver.resolvePath("/music/artist/album/track.mp3", nil)
+
+			Expect(resolution.valid).To(BeTrue())
+			Expect(resolution.libraryID).To(Equal(1))
+			Expect(resolution.libraryPath).To(Equal("/music"))
+			Expect(resolution.absolutePath).To(Equal("/music/artist/album/track.mp3"))
+		})
+
+		It("resolves relative paths when folder is provided", func() {
+			folder := &model.Folder{
+				Path:        "playlists",
+				LibraryPath: "/music",
+				LibraryID:   1,
+			}
+
+			resolution := resolver.resolvePath("../artist/album/track.mp3", folder)
+
+			Expect(resolution.valid).To(BeTrue())
+			Expect(resolution.libraryID).To(Equal(1))
+			Expect(resolution.absolutePath).To(Equal("/music/artist/album/track.mp3"))
+		})
+
+		It("returns invalid resolution for paths outside any library", func() {
+			resolution := resolver.resolvePath("/outside/library/track.mp3", nil)
+
+			Expect(resolution.valid).To(BeFalse())
+		})
+	})
+
+	Describe("resolvePath", func() {
+		Context("With absolute paths", func() {
+			It("resolves path within a library", func() {
+				resolution := resolver.resolvePath("/music/track.mp3", nil)
+
+				Expect(resolution.valid).To(BeTrue())
+				Expect(resolution.libraryID).To(Equal(1))
+				Expect(resolution.libraryPath).To(Equal("/music"))
+				Expect(resolution.absolutePath).To(Equal("/music/track.mp3"))
+			})
+
+			It("resolves path to the longest matching library", func() {
+				resolution := resolver.resolvePath("/music-classical/track.mp3", nil)
+
+				Expect(resolution.valid).To(BeTrue())
+				Expect(resolution.libraryID).To(Equal(2))
+				Expect(resolution.libraryPath).To(Equal("/music-classical"))
+			})
+
+			It("returns invalid resolution for path outside libraries", func() {
+				resolution := resolver.resolvePath("/videos/movie.mp4", nil)
+
+				Expect(resolution.valid).To(BeFalse())
+			})
+
+			It("cleans the path before matching", func() {
+				resolution := resolver.resolvePath("/music//artist/../artist/track.mp3", nil)
+
+				Expect(resolution.valid).To(BeTrue())
+				Expect(resolution.absolutePath).To(Equal("/music/artist/track.mp3"))
+			})
+		})
+
+		Context("With relative paths", func() {
+			It("resolves relative path within same library", func() {
+				folder := &model.Folder{
+					Path:        "playlists",
+					LibraryPath: "/music",
+					LibraryID:   1,
+				}
+
+				resolution := resolver.resolvePath("../songs/track.mp3", folder)
+
+				Expect(resolution.valid).To(BeTrue())
+				Expect(resolution.libraryID).To(Equal(1))
+				Expect(resolution.absolutePath).To(Equal("/music/songs/track.mp3"))
+			})
+
+			It("resolves relative path to different library", func() {
+				folder := &model.Folder{
+					Path:        "playlists",
+					LibraryPath: "/music",
+					LibraryID:   1,
+				}
+
+				// Path goes up and into a different library
+				resolution := resolver.resolvePath("../../podcasts/episode.mp3", folder)
+
+				Expect(resolution.valid).To(BeTrue())
+				Expect(resolution.libraryID).To(Equal(3))
+				Expect(resolution.libraryPath).To(Equal("/podcasts"))
+			})
+
+			It("uses matcher to find correct library for resolved path", func() {
+				folder := &model.Folder{
+					Path:        "playlists",
+					LibraryPath: "/music",
+					LibraryID:   1,
+				}
+
+				// This relative path resolves to music-classical library
+				resolution := resolver.resolvePath("../../music-classical/track.mp3", folder)
+
+				Expect(resolution.valid).To(BeTrue())
+				Expect(resolution.libraryID).To(Equal(2))
+				Expect(resolution.libraryPath).To(Equal("/music-classical"))
+			})
+
+			It("returns invalid for relative paths escaping all libraries", func() {
+				folder := &model.Folder{
+					Path:        "playlists",
+					LibraryPath: "/music",
+					LibraryID:   1,
+				}
+
+				resolution := resolver.resolvePath("../../../../etc/passwd", folder)
+
+				Expect(resolution.valid).To(BeFalse())
+			})
+		})
+	})
+
+	Describe("Cross-library resolution scenarios", func() {
+		It("handles playlist in library A referencing file in library B", func() {
+			// Playlist is in /music/playlists
+			folder := &model.Folder{
+				Path:        "playlists",
+				LibraryPath: "/music",
+				LibraryID:   1,
+			}
+
+			// Relative path that goes to /podcasts library
+			resolution := resolver.resolvePath("../../podcasts/show/episode.mp3", folder)
+
+			Expect(resolution.valid).To(BeTrue())
+			Expect(resolution.libraryID).To(Equal(3), "Should resolve to podcasts library")
+			Expect(resolution.libraryPath).To(Equal("/podcasts"))
+		})
+
+		It("prefers longer library paths when resolving", func() {
+			// Ensure /music-classical is matched instead of /music
+			resolution := resolver.resolvePath("/music-classical/baroque/track.mp3", nil)
+
+			Expect(resolution.valid).To(BeTrue())
+			Expect(resolution.libraryID).To(Equal(2), "Should match /music-classical, not /music")
+		})
+	})
+})
+
+var _ = Describe("pathResolution", func() {
+	Describe("ToQualifiedString", func() {
+		It("converts valid resolution to qualified string with forward slashes", func() {
+			resolution := pathResolution{
+				absolutePath: "/music/artist/album/track.mp3",
+				libraryPath:  "/music",
+				libraryID:    1,
+				valid:        true,
+			}
+
+			qualifiedStr, err := resolution.ToQualifiedString()
+
+			Expect(err).ToNot(HaveOccurred())
+			Expect(qualifiedStr).To(Equal("1:artist/album/track.mp3"))
+		})
+
+		It("handles Windows-style paths by converting to forward slashes", func() {
+			resolution := pathResolution{
+				absolutePath: "/music/artist/album/track.mp3",
+				libraryPath:  "/music",
+				libraryID:    2,
+				valid:        true,
+			}
+
+			qualifiedStr, err := resolution.ToQualifiedString()
+
+			Expect(err).ToNot(HaveOccurred())
+			// Should always use forward slashes regardless of OS
+			Expect(qualifiedStr).To(ContainSubstring("2:"))
+			Expect(qualifiedStr).ToNot(ContainSubstring("\\"))
+		})
+
+		It("returns error for invalid resolution", func() {
+			resolution := pathResolution{valid: false}
+
+			_, err := resolution.ToQualifiedString()
+
+			Expect(err).To(HaveOccurred())
+		})
+	})
+})
diff --git a/core/playlists_test.go b/core/playlists_test.go
index fb42f9c9f..6aa8aac9a 100644
--- a/core/playlists_test.go
+++ b/core/playlists_test.go
@@ -1,4 +1,4 @@
-package core
+package core_test
 
 import (
 	"context"
@@ -9,6 +9,7 @@ import (
 
 	"github.com/navidrome/navidrome/conf"
 	"github.com/navidrome/navidrome/conf/configtest"
+	"github.com/navidrome/navidrome/core"
 	"github.com/navidrome/navidrome/model"
 	"github.com/navidrome/navidrome/model/criteria"
 	"github.com/navidrome/navidrome/model/request"
@@ -20,7 +21,7 @@ import (
 
 var _ = Describe("Playlists", func() {
 	var ds *tests.MockDataStore
-	var ps Playlists
+	var ps core.Playlists
 	var mockPlsRepo mockedPlaylistRepo
 	var mockLibRepo *tests.MockLibraryRepo
 	ctx := context.Background()
@@ -33,16 +34,16 @@ var _ = Describe("Playlists", func() {
 			MockedLibrary:  mockLibRepo,
 		}
 		ctx = request.WithUser(ctx, model.User{ID: "123"})
-		// Path should be libPath, but we want to match the root folder referenced in the m3u, which is `/`
-		mockLibRepo.SetData([]model.Library{{ID: 1, Path: "/"}})
 	})
 
 	Describe("ImportFile", func() {
 		var folder *model.Folder
 		BeforeEach(func() {
-			ps = NewPlaylists(ds)
+			ps = core.NewPlaylists(ds)
 			ds.MockedMediaFile = &mockedMediaFileRepo{}
 			libPath, _ := os.Getwd()
+			// Set up library with the actual library path that matches the folder
+			mockLibRepo.SetData([]model.Library{{ID: 1, Path: libPath}})
 			folder = &model.Folder{
 				ID:          "1",
 				LibraryID:   1,
@@ -112,6 +113,224 @@ var _ = Describe("Playlists", func() {
 				Expect(err.Error()).To(ContainSubstring("line 19, column 1: invalid character '\\n'"))
 			})
 		})
+
+		Describe("Cross-library relative paths", func() {
+			var tmpDir, plsDir, songsDir string
+
+			BeforeEach(func() {
+				// Create temp directory structure
+				tmpDir = GinkgoT().TempDir()
+				plsDir = tmpDir + "/playlists"
+				songsDir = tmpDir + "/songs"
+				Expect(os.Mkdir(plsDir, 0755)).To(Succeed())
+				Expect(os.Mkdir(songsDir, 0755)).To(Succeed())
+
+				// Setup two different libraries with paths matching our temp structure
+				mockLibRepo.SetData([]model.Library{
+					{ID: 1, Path: songsDir},
+					{ID: 2, Path: plsDir},
+				})
+
+				// Create a mock media file repository that returns files for both libraries
+				// Note: The paths are relative to their respective library roots
+				ds.MockedMediaFile = &mockedMediaFileFromListRepo{
+					data: []string{
+						"abc.mp3", // This is songs/abc.mp3 relative to songsDir
+						"def.mp3", // This is playlists/def.mp3 relative to plsDir
+					},
+				}
+				ps = core.NewPlaylists(ds)
+			})
+
+			It("handles relative paths that reference files in other libraries", func() {
+				// Create a temporary playlist file with relative path
+				plsContent := "#PLAYLIST:Cross Library Test\n../songs/abc.mp3\ndef.mp3"
+				plsFile := plsDir + "/test.m3u"
+				Expect(os.WriteFile(plsFile, []byte(plsContent), 0600)).To(Succeed())
+
+				// Playlist is in the Playlists library folder
+				// Important: Path should be relative to LibraryPath, and Name is the folder name
+				plsFolder := &model.Folder{
+					ID:          "2",
+					LibraryID:   2,
+					LibraryPath: plsDir,
+					Path:        "",
+					Name:        "",
+				}
+
+				pls, err := ps.ImportFile(ctx, plsFolder, "test.m3u")
+				Expect(err).ToNot(HaveOccurred())
+				Expect(pls.Tracks).To(HaveLen(2))
+				Expect(pls.Tracks[0].Path).To(Equal("abc.mp3")) // From songsDir library
+				Expect(pls.Tracks[1].Path).To(Equal("def.mp3")) // From plsDir library
+			})
+
+			It("ignores paths that point outside all libraries", func() {
+				// Create a temporary playlist file with path outside libraries
+				plsContent := "#PLAYLIST:Outside Test\n../../outside.mp3\nabc.mp3"
+				plsFile := plsDir + "/test.m3u"
+				Expect(os.WriteFile(plsFile, []byte(plsContent), 0600)).To(Succeed())
+
+				plsFolder := &model.Folder{
+					ID:          "2",
+					LibraryID:   2,
+					LibraryPath: plsDir,
+					Path:        "",
+					Name:        "",
+				}
+
+				pls, err := ps.ImportFile(ctx, plsFolder, "test.m3u")
+				Expect(err).ToNot(HaveOccurred())
+				// Should only find abc.mp3, not outside.mp3
+				Expect(pls.Tracks).To(HaveLen(1))
+				Expect(pls.Tracks[0].Path).To(Equal("abc.mp3"))
+			})
+
+			It("handles relative paths with multiple '../' components", func() {
+				// Create a nested structure: tmpDir/playlists/subfolder/test.m3u
+				subFolder := plsDir + "/subfolder"
+				Expect(os.Mkdir(subFolder, 0755)).To(Succeed())
+
+				// Create the media file in the subfolder directory
+				// The mock will return it as "def.mp3" relative to plsDir
+				ds.MockedMediaFile = &mockedMediaFileFromListRepo{
+					data: []string{
+						"abc.mp3", // From songsDir library
+						"def.mp3", // From plsDir library root
+					},
+				}
+
+				// From subfolder, ../../songs/abc.mp3 should resolve to songs library
+				// ../def.mp3 should resolve to plsDir/def.mp3
+				plsContent := "#PLAYLIST:Nested Test\n../../songs/abc.mp3\n../def.mp3"
+				plsFile := subFolder + "/test.m3u"
+				Expect(os.WriteFile(plsFile, []byte(plsContent), 0600)).To(Succeed())
+
+				// The folder: AbsolutePath = LibraryPath + Path + Name
+				// So for /playlists/subfolder: LibraryPath=/playlists, Path="", Name="subfolder"
+				plsFolder := &model.Folder{
+					ID:          "2",
+					LibraryID:   2,
+					LibraryPath: plsDir,
+					Path:        "",          // Empty because subfolder is directly under library root
+					Name:        "subfolder", // The folder name
+				}
+
+				pls, err := ps.ImportFile(ctx, plsFolder, "test.m3u")
+				Expect(err).ToNot(HaveOccurred())
+				Expect(pls.Tracks).To(HaveLen(2))
+				Expect(pls.Tracks[0].Path).To(Equal("abc.mp3")) // From songsDir library
+				Expect(pls.Tracks[1].Path).To(Equal("def.mp3")) // From plsDir library root
+			})
+
+			It("correctly resolves libraries when one path is a prefix of another", func() {
+				// This tests the bug where /music would match before /music-classical
+				// Create temp directory structure with prefix conflict
+				tmpDir := GinkgoT().TempDir()
+				musicDir := tmpDir + "/music"
+				musicClassicalDir := tmpDir + "/music-classical"
+				Expect(os.Mkdir(musicDir, 0755)).To(Succeed())
+				Expect(os.Mkdir(musicClassicalDir, 0755)).To(Succeed())
+
+				// Setup two libraries where one is a prefix of the other
+				mockLibRepo.SetData([]model.Library{
+					{ID: 1, Path: musicDir},          // /tmp/xxx/music
+					{ID: 2, Path: musicClassicalDir}, // /tmp/xxx/music-classical
+				})
+
+				// Mock will return tracks from both libraries
+				ds.MockedMediaFile = &mockedMediaFileFromListRepo{
+					data: []string{
+						"rock.mp3", // From music library
+						"bach.mp3", // From music-classical library
+					},
+				}
+
+				// Create playlist in music library that references music-classical
+				plsContent := "#PLAYLIST:Cross Prefix Test\nrock.mp3\n../music-classical/bach.mp3"
+				plsFile := musicDir + "/test.m3u"
+				Expect(os.WriteFile(plsFile, []byte(plsContent), 0600)).To(Succeed())
+
+				plsFolder := &model.Folder{
+					ID:          "1",
+					LibraryID:   1,
+					LibraryPath: musicDir,
+					Path:        "",
+					Name:        "",
+				}
+
+				pls, err := ps.ImportFile(ctx, plsFolder, "test.m3u")
+				Expect(err).ToNot(HaveOccurred())
+				Expect(pls.Tracks).To(HaveLen(2))
+				Expect(pls.Tracks[0].Path).To(Equal("rock.mp3")) // From music library
+				Expect(pls.Tracks[1].Path).To(Equal("bach.mp3")) // From music-classical library (not music!)
+			})
+
+			It("correctly handles identical relative paths from different libraries", func() {
+				// This tests the bug where two libraries have files at the same relative path
+				// and only one appears in the playlist
+				tmpDir := GinkgoT().TempDir()
+				musicDir := tmpDir + "/music"
+				classicalDir := tmpDir + "/classical"
+				Expect(os.Mkdir(musicDir, 0755)).To(Succeed())
+				Expect(os.Mkdir(classicalDir, 0755)).To(Succeed())
+				Expect(os.MkdirAll(musicDir+"/album", 0755)).To(Succeed())
+				Expect(os.MkdirAll(classicalDir+"/album", 0755)).To(Succeed())
+				// Create placeholder files so paths resolve correctly
+				Expect(os.WriteFile(musicDir+"/album/track.mp3", []byte{}, 0600)).To(Succeed())
+				Expect(os.WriteFile(classicalDir+"/album/track.mp3", []byte{}, 0600)).To(Succeed())
+
+				// Both libraries have a file at "album/track.mp3"
+				mockLibRepo.SetData([]model.Library{
+					{ID: 1, Path: musicDir},
+					{ID: 2, Path: classicalDir},
+				})
+
+				// Mock returns files with same relative path but different IDs and library IDs
+				// Keys use the library-qualified format: "libraryID:path"
+				ds.MockedMediaFile = &mockedMediaFileRepo{
+					data: map[string]model.MediaFile{
+						"1:album/track.mp3": {ID: "music-track", Path: "album/track.mp3", LibraryID: 1, Title: "Rock Song"},
+						"2:album/track.mp3": {ID: "classical-track", Path: "album/track.mp3", LibraryID: 2, Title: "Classical Piece"},
+					},
+				}
+				// Recreate playlists service to pick up new mock
+				ps = core.NewPlaylists(ds)
+
+				// Create playlist in music library that references both tracks
+				plsContent := "#PLAYLIST:Same Path Test\nalbum/track.mp3\n../classical/album/track.mp3"
+				plsFile := musicDir + "/test.m3u"
+				Expect(os.WriteFile(plsFile, []byte(plsContent), 0600)).To(Succeed())
+
+				plsFolder := &model.Folder{
+					ID:          "1",
+					LibraryID:   1,
+					LibraryPath: musicDir,
+					Path:        "",
+					Name:        "",
+				}
+
+				pls, err := ps.ImportFile(ctx, plsFolder, "test.m3u")
+				Expect(err).ToNot(HaveOccurred())
+
+				// Should have BOTH tracks, not just one
+				Expect(pls.Tracks).To(HaveLen(2), "Playlist should contain both tracks with same relative path")
+
+				// Verify we got tracks from DIFFERENT libraries (the key fix!)
+				// Collect the library IDs
+				libIDs := make(map[int]bool)
+				for _, track := range pls.Tracks {
+					libIDs[track.LibraryID] = true
+				}
+				Expect(libIDs).To(HaveLen(2), "Tracks should come from two different libraries")
+				Expect(libIDs[1]).To(BeTrue(), "Should have track from library 1")
+				Expect(libIDs[2]).To(BeTrue(), "Should have track from library 2")
+
+				// Both tracks should have the same relative path
+				Expect(pls.Tracks[0].Path).To(Equal("album/track.mp3"))
+				Expect(pls.Tracks[1].Path).To(Equal("album/track.mp3"))
+			})
+		})
 	})
 
 	Describe("ImportM3U", func() {
@@ -119,7 +338,7 @@ var _ = Describe("Playlists", func() {
 		BeforeEach(func() {
 			repo = &mockedMediaFileFromListRepo{}
 			ds.MockedMediaFile = repo
-			ps = NewPlaylists(ds)
+			ps = core.NewPlaylists(ds)
 			mockLibRepo.SetData([]model.Library{{ID: 1, Path: "/music"}, {ID: 2, Path: "/new"}})
 			ctx = request.WithUser(ctx, model.User{ID: "123"})
 		})
@@ -206,53 +425,23 @@ var _ = Describe("Playlists", func() {
 			Expect(pls.Tracks[0].Path).To(Equal("abc/tEsT1.Mp3"))
 		})
 
-		It("handles Unicode normalization when comparing paths", func() {
-			// Test case for Apple Music playlists that use NFC encoding vs macOS filesystem NFD
-			// The character "è" can be represented as NFC (single codepoint) or NFD (e + combining accent)
-
-			const pathWithAccents = "artist/Michèle Desrosiers/album/Noël.m4a"
-
-			// Simulate a database entry with NFD encoding (as stored by macOS filesystem)
-			nfdPath := norm.NFD.String(pathWithAccents)
+		It("handles Unicode normalization when comparing paths (NFD vs NFC)", func() {
+			// Simulate macOS filesystem: stores paths in NFD (decomposed) form
+			// "è" (U+00E8) in NFC becomes "e" + "◌̀" (U+0065 + U+0300) in NFD
+			nfdPath := "artist/Mich" + string([]rune{'e', '\u0300'}) + "le/song.mp3" // NFD: e + combining grave
 			repo.data = []string{nfdPath}
 
-			// Simulate an Apple Music M3U playlist entry with NFC encoding
-			nfcPath := norm.NFC.String("/music/" + pathWithAccents)
-			m3u := strings.Join([]string{
-				nfcPath,
-			}, "\n")
+			// Simulate Apple Music M3U: uses NFC (composed) form
+			nfcPath := "/music/artist/Mich\u00E8le/song.mp3" // NFC: single è character
+			m3u := nfcPath + "\n"
 			f := strings.NewReader(m3u)
-
 			pls, err := ps.ImportM3U(ctx, f)
 			Expect(err).ToNot(HaveOccurred())
-			Expect(pls.Tracks).To(HaveLen(1), "Should find the track despite Unicode normalization differences")
+			Expect(pls.Tracks).To(HaveLen(1))
+			// Should match despite different Unicode normalization forms
 			Expect(pls.Tracks[0].Path).To(Equal(nfdPath))
 		})
-	})
 
-	Describe("normalizePathForComparison", func() {
-		It("normalizes Unicode characters to NFC form and converts to lowercase", func() {
-			// Test with NFD (decomposed) input - as would come from macOS filesystem
-			nfdPath := norm.NFD.String("Michèle") // Explicitly convert to NFD form
-			normalized := normalizePathForComparison(nfdPath)
-			Expect(normalized).To(Equal("michèle"))
-
-			// Test with NFC (composed) input - as would come from Apple Music M3U
-			nfcPath := "Michèle" // This might be in NFC form
-			normalizedNfc := normalizePathForComparison(nfcPath)
-
-			// Ensure the two paths are not equal in their original forms
-			Expect(nfdPath).ToNot(Equal(nfcPath))
-
-			// Both should normalize to the same result
-			Expect(normalized).To(Equal(normalizedNfc))
-		})
-
-		It("handles paths with mixed case and Unicode characters", func() {
-			path := "Artist/Noël Coward/Album/Song.mp3"
-			normalized := normalizePathForComparison(path)
-			Expect(normalized).To(Equal("artist/noël coward/album/song.mp3"))
-		})
 	})
 
 	Describe("InPlaylistsPath", func() {
@@ -269,27 +458,27 @@ var _ = Describe("Playlists", func() {
 
 		It("returns true if PlaylistsPath is empty", func() {
 			conf.Server.PlaylistsPath = ""
-			Expect(InPlaylistsPath(folder)).To(BeTrue())
+			Expect(core.InPlaylistsPath(folder)).To(BeTrue())
 		})
 
 		It("returns true if PlaylistsPath is any (**/**)", func() {
 			conf.Server.PlaylistsPath = "**/**"
-			Expect(InPlaylistsPath(folder)).To(BeTrue())
+			Expect(core.InPlaylistsPath(folder)).To(BeTrue())
 		})
 
 		It("returns true if folder is in PlaylistsPath", func() {
 			conf.Server.PlaylistsPath = "other/**:playlists/**"
-			Expect(InPlaylistsPath(folder)).To(BeTrue())
+			Expect(core.InPlaylistsPath(folder)).To(BeTrue())
 		})
 
 		It("returns false if folder is not in PlaylistsPath", func() {
 			conf.Server.PlaylistsPath = "other"
-			Expect(InPlaylistsPath(folder)).To(BeFalse())
+			Expect(core.InPlaylistsPath(folder)).To(BeFalse())
 		})
 
 		It("returns true if for a playlist in root of MusicFolder if PlaylistsPath is '.'", func() {
 			conf.Server.PlaylistsPath = "."
-			Expect(InPlaylistsPath(folder)).To(BeFalse())
+			Expect(core.InPlaylistsPath(folder)).To(BeFalse())
 
 			folder2 := model.Folder{
 				LibraryPath: "/music",
@@ -297,22 +486,47 @@ var _ = Describe("Playlists", func() {
 				Name:        ".",
 			}
 
-			Expect(InPlaylistsPath(folder2)).To(BeTrue())
+			Expect(core.InPlaylistsPath(folder2)).To(BeTrue())
 		})
 	})
 })
 
-// mockedMediaFileRepo's FindByPaths method returns a list of MediaFiles with the same paths as the input
+// mockedMediaFileRepo's FindByPaths method returns MediaFiles for the given paths.
+// If data map is provided, looks up files by key; otherwise creates them from paths.
 type mockedMediaFileRepo struct {
 	model.MediaFileRepository
+	data map[string]model.MediaFile
 }
 
 func (r *mockedMediaFileRepo) FindByPaths(paths []string) (model.MediaFiles, error) {
 	var mfs model.MediaFiles
+
+	// If data map provided, look up files
+	if r.data != nil {
+		for _, path := range paths {
+			if mf, ok := r.data[path]; ok {
+				mfs = append(mfs, mf)
+			}
+		}
+		return mfs, nil
+	}
+
+	// Otherwise, create MediaFiles from paths
 	for idx, path := range paths {
+		// Strip library qualifier if present (format: "libraryID:path")
+		actualPath := path
+		libraryID := 1
+		if parts := strings.SplitN(path, ":", 2); len(parts) == 2 {
+			if id, err := strconv.Atoi(parts[0]); err == nil {
+				libraryID = id
+				actualPath = parts[1]
+			}
+		}
+
 		mfs = append(mfs, model.MediaFile{
-			ID:   strconv.Itoa(idx),
-			Path: path,
+			ID:        strconv.Itoa(idx),
+			Path:      actualPath,
+			LibraryID: libraryID,
 		})
 	}
 	return mfs, nil
@@ -324,13 +538,38 @@ type mockedMediaFileFromListRepo struct {
 	data []string
 }
 
-func (r *mockedMediaFileFromListRepo) FindByPaths([]string) (model.MediaFiles, error) {
+func (r *mockedMediaFileFromListRepo) FindByPaths(paths []string) (model.MediaFiles, error) {
 	var mfs model.MediaFiles
-	for idx, path := range r.data {
-		mfs = append(mfs, model.MediaFile{
-			ID:   strconv.Itoa(idx),
-			Path: path,
-		})
+
+	for idx, dataPath := range r.data {
+		// Normalize the data path to NFD (simulates macOS filesystem storage)
+		normalizedDataPath := norm.NFD.String(dataPath)
+
+		for _, requestPath := range paths {
+			// Strip library qualifier if present (format: "libraryID:path")
+			actualPath := requestPath
+			libraryID := 1
+			if parts := strings.SplitN(requestPath, ":", 2); len(parts) == 2 {
+				if id, err := strconv.Atoi(parts[0]); err == nil {
+					libraryID = id
+					actualPath = parts[1]
+				}
+			}
+
+			// The request path should already be normalized to NFD by production code
+			// before calling FindByPaths (to match DB storage)
+			normalizedRequestPath := norm.NFD.String(actualPath)
+
+			// Case-insensitive comparison (like SQL's "collate nocase")
+			if strings.EqualFold(normalizedRequestPath, normalizedDataPath) {
+				mfs = append(mfs, model.MediaFile{
+					ID:        strconv.Itoa(idx),
+					Path:      dataPath, // Return original path from DB
+					LibraryID: libraryID,
+				})
+				break
+			}
+		}
 	}
 	return mfs, nil
 }
diff --git a/persistence/mediafile_repository.go b/persistence/mediafile_repository.go
index 8f32accc6..4749bb0be 100644
--- a/persistence/mediafile_repository.go
+++ b/persistence/mediafile_repository.go
@@ -4,6 +4,8 @@ import (
 	"context"
 	"fmt"
 	"slices"
+	"strconv"
+	"strings"
 	"sync"
 	"time"
 
@@ -193,12 +195,43 @@ func (r *mediaFileRepository) GetCursor(options ...model.QueryOptions) (model.Me
 	}, nil
 }
 
+// FindByPaths finds media files by their paths.
+// The paths can be library-qualified (format: "libraryID:path") or unqualified ("path").
+// Library-qualified paths search within the specified library, while unqualified paths
+// search across all libraries for backward compatibility.
 func (r *mediaFileRepository) FindByPaths(paths []string) (model.MediaFiles, error) {
-	sel := r.newSelect().Columns("*").Where(Eq{"path collate nocase": paths})
+	query := Or{}
+
+	for _, path := range paths {
+		parts := strings.SplitN(path, ":", 2)
+		if len(parts) == 2 {
+			// Library-qualified path: "libraryID:path"
+			libraryID, err := strconv.Atoi(parts[0])
+			if err != nil {
+				// Invalid format, skip
+				continue
+			}
+			relativePath := parts[1]
+			query = append(query, And{
+				Eq{"path collate nocase": relativePath},
+				Eq{"library_id": libraryID},
+			})
+		} else {
+			// Unqualified path: search across all libraries
+			query = append(query, Eq{"path collate nocase": path})
+		}
+	}
+
+	if len(query) == 0 {
+		return model.MediaFiles{}, nil
+	}
+
+	sel := r.newSelect().Columns("*").Where(query)
 	var res dbMediaFiles
 	if err := r.queryAll(sel, &res); err != nil {
 		return nil, err
 	}
+
 	return res.toModels(), nil
 }