diff --git a/booklore-api/src/main/java/com/adityachandel/booklore/util/PathPatternResolver.java b/booklore-api/src/main/java/com/adityachandel/booklore/util/PathPatternResolver.java
index ccbab241..f355c7bb 100644
--- a/booklore-api/src/main/java/com/adityachandel/booklore/util/PathPatternResolver.java
+++ b/booklore-api/src/main/java/com/adityachandel/booklore/util/PathPatternResolver.java
@@ -266,6 +266,9 @@ public class PathPatternResolver {
                 if (component.getBytes(StandardCharsets.UTF_8).length > MAX_FILESYSTEM_COMPONENT_BYTES) {
                     component = truncatePathComponent(component, MAX_FILESYSTEM_COMPONENT_BYTES);
                 }
+                while (component.endsWith(".")) {
+                    component = component.substring(0, component.length() - 1);
+                }
             }
 
             if (i > 0) result.append("/");
diff --git a/booklore-api/src/test/java/com/adityachandel/booklore/util/PathPatternResolverTest.java b/booklore-api/src/test/java/com/adityachandel/booklore/util/PathPatternResolverTest.java
index 83ae2783..55c70ab7 100644
--- a/booklore-api/src/test/java/com/adityachandel/booklore/util/PathPatternResolverTest.java
+++ b/booklore-api/src/test/java/com/adityachandel/booklore/util/PathPatternResolverTest.java
@@ -467,4 +467,47 @@ class PathPatternResolverTest {
         int byteLen = result.getBytes(StandardCharsets.UTF_8).length;
         assertTrue(byteLen <= 245, "Total filename bytes " + byteLen + " should be <= 245");
     }
+
+    @Test
+    @DisplayName("Should remove trailing dots from path components for Windows compatibility")
+    void testResolvePattern_removesTrailingDots() {
+        BookMetadata metadata = BookMetadata.builder()
+                .title("Book Title")
+                .authors(Set.of("Author Name Jr."))
+                .build();
+
+        // Pattern: {authors}/{title}
+        String result = PathPatternResolver.resolvePattern(metadata, "{authors}/{title}", "original.pdf");
+
+        // Expected: Author Name Jr/Book Title.pdf
+        // Windows does not allow folder names ending in '.'
+        // So "Author Name Jr." should become "Author Name Jr"
+
+        String[] components = result.split("/");
+        assertTrue(components.length >= 1);
+
+        String authorDir = components[0];
+        assertFalse(authorDir.endsWith("."), "Directory name should not end with a dot: " + authorDir);
+        assertTrue(authorDir.equals("Author Name Jr"), "Expected 'Author Name Jr' but got '" + authorDir + "'");
+    }
+
+    @Test
+    @DisplayName("Should remove trailing dots from multiple path components")
+    void testResolvePattern_removesTrailingDotsFromMultipleComponents() {
+        BookMetadata metadata = BookMetadata.builder()
+                .title("Book Title.")
+                .seriesName("Series.")
+                .authors(Set.of("Author."))
+                .build();
+
+        String result = PathPatternResolver.resolvePattern(metadata, "{authors}/{series}/{title}", "original.pdf");
+
+        String[] components = result.split("/");
+        for (int i = 0; i < components.length - 1; i++) { // Check directories
+            assertFalse(components[i].endsWith("."), "Component " + i + " should not end with dot: " + components[i]);
+        }
+
+        assertTrue(components[0].equals("Author"));
+        assertTrue(components[1].equals("Series"));
+    }
 }