diff --git a/src/main/kotlin/com/jetpackduba/gitnuro/ui/tree_files/Tree.kt b/src/main/kotlin/com/jetpackduba/gitnuro/ui/tree_files/Tree.kt
index 4c3256c9..48652c95 100644
--- a/src/main/kotlin/com/jetpackduba/gitnuro/ui/tree_files/Tree.kt
+++ b/src/main/kotlin/com/jetpackduba/gitnuro/ui/tree_files/Tree.kt
@@ -1,6 +1,8 @@
 package com.jetpackduba.gitnuro.ui.tree_files
 
+import arrow.core.compareTo
 import com.jetpackduba.gitnuro.system.systemSeparator
+import kotlin.math.max
 
 fun <T> entriesToTreeEntry(
     entries: List<T>,
@@ -9,20 +11,26 @@ fun <T> entriesToTreeEntry(
 ): List<TreeItem<T>> {
     return entries
         .asSequence()
+        .sortedWith { entry1, entry2 ->
+            val path1 = onGetEntryPath(entry1)
+            val path2 = onGetEntryPath(entry2)
+
+            PathsComparator().compare(path1, path2)
+        }
         .map { entry ->
             val filePath = onGetEntryPath(entry)
             val parts = filePath.split(systemSeparator)
 
             parts.mapIndexed { index, partName ->
                 if (index == parts.lastIndex) {
-                    val isParentContracted = treeContractedDirs.none { contractedDir ->
+                    val isParentDirectoryContracted = treeContractedDirs.any { contractedDir ->
                         filePath.startsWith(contractedDir + systemSeparator)
                     }
 
-                    if (isParentContracted) {
-                        TreeItem.File(entry, partName, filePath, index)
-                    } else {
+                    if (isParentDirectoryContracted) {
                         null
+                    } else {
+                        TreeItem.File(entry, partName, filePath, index)
                     }
                 } else {
                     val dirPath = parts.slice(0..index).joinToString(systemSeparator)
@@ -45,10 +53,34 @@ fun <T> entriesToTreeEntry(
         .flatten()
         .filterNotNull()
         .distinct()
-        .sortedBy { it.fullPath }
         .toList()
 }
 
+private class PathsComparator : Comparator<String> {
+    override fun compare(path1: String, path2: String): Int {
+        val path1Parts = path1.split(systemSeparator)
+        val path2Parts = path2.split(systemSeparator)
+
+        path1Parts.compareTo(path2Parts)
+
+        val maxIndex = max(path1Parts.count(), path2Parts.count())
+
+        for (i in 0 until maxIndex) {
+            val part1 = path1Parts.getOrNull(i) ?: return -1
+            val part2 = path2Parts.getOrNull(i) ?: return 1
+
+            val comparison = part1.compareTo(part2)
+
+            if (comparison != 0) {
+                return comparison
+            }
+        }
+
+        return 0
+    }
+
+}
+
 sealed interface TreeItem<out T> {
     val fullPath: String
     val displayName: String
diff --git a/src/test/kotlin/com/jetpackduba/gitnuro/ui/tree_files/TreeTest.kt b/src/test/kotlin/com/jetpackduba/gitnuro/ui/tree_files/TreeTest.kt
new file mode 100644
index 00000000..5b6d737d
--- /dev/null
+++ b/src/test/kotlin/com/jetpackduba/gitnuro/ui/tree_files/TreeTest.kt
@@ -0,0 +1,80 @@
+package com.jetpackduba.gitnuro.ui.tree_files
+
+import org.junit.jupiter.api.Assertions.assertEquals
+import org.junit.jupiter.api.Assertions.assertTrue
+import org.junit.jupiter.api.Test
+
+class TreeTest {
+
+    @Test
+    fun `test entriesToTreeEntry with empty entries`() {
+        val entries = emptyList<String>()
+        val treeContractedDirs = emptyList<String>()
+        val result = entriesToTreeEntry(entries, treeContractedDirs) { it }
+        assertTrue(result.isEmpty())
+    }
+
+    @Test
+    fun `test entriesToTreeEntry with single file entry`() {
+        val entries = listOf("file.txt")
+        val treeContractedDirs = emptyList<String>()
+        val result = entriesToTreeEntry(entries, treeContractedDirs) { it }
+
+        assertEquals(listOf(TreeItem.File("file.txt", "file.txt", "file.txt", 0)), result)
+    }
+
+    @Test
+    fun `test entriesToTreeEntry with multiple file entries`() {
+        val entries = listOf("dir1/file1.txt", "dir2/file2.txt", "dir3/file3.txt")
+        val treeContractedDirs = emptyList<String>()
+        val result = entriesToTreeEntry(entries, treeContractedDirs) { it }
+        val expected = listOf(
+            TreeItem.Dir(true, "dir1", "dir1", 0),
+            TreeItem.File("dir1/file1.txt", "file1.txt", "dir1/file1.txt", 1),
+            TreeItem.Dir(true, "dir2", "dir2", 0),
+            TreeItem.File("dir2/file2.txt", "file2.txt", "dir2/file2.txt", 1),
+            TreeItem.Dir(true, "dir3", "dir3", 0),
+            TreeItem.File("dir3/file3.txt", "file3.txt", "dir3/file3.txt", 1)
+        )
+        assertEquals(expected, result)
+    }
+
+    @Test
+    fun `test entriesToTreeEntry with similar names`() {
+        val entries = listOf(
+            "webpack/webpack.config2.ts",
+            "webpack/webpack.config.ts",
+            "webpack-plugin.ts",
+            "dir1/file3.txt"
+        )
+        val treeContractedDirs = emptyList<String>()
+        val result = entriesToTreeEntry(entries, treeContractedDirs) { it }
+        val expected = listOf(
+            TreeItem.Dir(true, "dir1", "dir1", 0),
+            TreeItem.File("dir1/file3.txt", "file3.txt", "dir1/file3.txt", 1),
+            TreeItem.Dir(true, "webpack", "webpack", 0),
+            TreeItem.File("webpack/webpack.config.ts", "webpack.config.ts", "webpack/webpack.config.ts", 1),
+            TreeItem.File("webpack/webpack.config2.ts", "webpack.config2.ts", "webpack/webpack.config2.ts", 1),
+            TreeItem.File("webpack-plugin.ts", "webpack-plugin.ts", "webpack-plugin.ts", 0)
+        )
+        assertEquals(expected, result)
+    }
+
+    @Test
+    fun `test entriesToTreeEntry with contracted directories`() {
+        val entries = listOf(
+            "webpack/webpack.config2.ts",
+            "webpack/webpack.config.ts",
+            "webpack-plugin.ts",
+            "dir1/file3.txt"
+        )
+        val treeContractedDirs = listOf<String>("webpack", "dir1")
+        val result = entriesToTreeEntry(entries, treeContractedDirs) { it }
+        val expected = listOf(
+            TreeItem.Dir(false, "dir1", "dir1", 0),
+            TreeItem.Dir(false, "webpack", "webpack", 0),
+            TreeItem.File("webpack-plugin.ts", "webpack-plugin.ts", "webpack-plugin.ts", 0)
+        )
+        assertEquals(expected, result)
+    }
+}
\ No newline at end of file