diff --git a/src/main/ipc/filesystem.ts b/src/main/ipc/filesystem.ts
index 466166cfcad..06a34e6eb5a 100644
--- a/src/main/ipc/filesystem.ts
+++ b/src/main/ipc/filesystem.ts
@@ -30,6 +30,7 @@ import type {
 } from '../../shared/types'
 import type { GitHistoryOptions, GitHistoryResult } from '../../shared/git-history'
 import type { SshMutationExpectation } from '../../shared/ssh-types'
+import { compareFileNames } from '../../shared/file-name-sort'
 import { assertSshMutationExpectation } from '../ssh/ssh-connection-generation'
 import {
   buildRgArgs,
@@ -531,7 +532,7 @@ export function registerFilesystemHandlers(
           if (a.isDirectory !== b.isDirectory) {
             return a.isDirectory ? -1 : 1
           }
-          return a.name.localeCompare(b.name)
+          return compareFileNames(a.name, b.name)
         })
       } catch (error: unknown) {
         recordCrashBreadcrumb(
diff --git a/src/main/runtime/orca-runtime-files.ts b/src/main/runtime/orca-runtime-files.ts
index 1ea6769ff4c..2ab0e0b9cc8 100644
--- a/src/main/runtime/orca-runtime-files.ts
+++ b/src/main/runtime/orca-runtime-files.ts
@@ -38,6 +38,7 @@ import {
   resolveRuntimePath
 } from '../../shared/cross-platform-path'
 import { PhysicalExitTracker } from '../../shared/physical-exit-tracker'
+import { compareFileNames } from '../../shared/file-name-sort'
 import type {
   RuntimeFileListResult,
   RuntimeFileOpenResult,
@@ -1277,7 +1278,7 @@ export class RuntimeFileCommands {
       if (a.isDirectory !== b.isDirectory) {
         return a.isDirectory ? -1 : 1
       }
-      return a.name.localeCompare(b.name)
+      return compareFileNames(a.name, b.name)
     })
   }
 
diff --git a/src/renderer/src/components/right-sidebar/file-explorer-name-filter-projection.ts b/src/renderer/src/components/right-sidebar/file-explorer-name-filter-projection.ts
index ba057328924..9070472ed0c 100644
--- a/src/renderer/src/components/right-sidebar/file-explorer-name-filter-projection.ts
+++ b/src/renderer/src/components/right-sidebar/file-explorer-name-filter-projection.ts
@@ -1,5 +1,6 @@
 import { joinPath, normalizeRelativePath } from '@/lib/path'
 import { isClipboardTextByteLengthOverLimit } from '../../../../shared/clipboard-text'
+import { compareFileNames } from '../../../../shared/file-name-sort'
 import type { FileExplorerOperationOwner, TreeNode } from './file-explorer-types'
 import {
   createFileExplorerRowProjectionFromParts,
@@ -232,7 +233,7 @@ function appendNameFilteredEntries(
     if (a.node.isDirectory !== b.node.isDirectory) {
       return a.node.isDirectory ? -1 : 1
     }
-    return a.node.name.localeCompare(b.node.name)
+    return compareFileNames(a.node.name, b.node.name)
   })
   for (const entry of sortedEntries) {
     visibleFlatRows.push(entry.node)
diff --git a/src/renderer/src/components/right-sidebar/source-control-status-sort.ts b/src/renderer/src/components/right-sidebar/source-control-status-sort.ts
index f5ee065bc70..f22f340a855 100644
--- a/src/renderer/src/components/right-sidebar/source-control-status-sort.ts
+++ b/src/renderer/src/components/right-sidebar/source-control-status-sort.ts
@@ -1,8 +1,7 @@
 import type { GitStatusEntry } from '../../../../shared/types'
+import { fileNameCollator } from '../../../../shared/file-name-sort'
 
-// Why hoisted: localeCompare with an options object resolves a fresh ICU collator
-// on every comparison, so a changed-file sort paid for one per O(n log n) step.
-export const sourceControlPathCollator = new Intl.Collator(undefined, { numeric: true })
+export const sourceControlPathCollator = fileNameCollator
 
 export function compareGitStatusEntries(a: GitStatusEntry, b: GitStatusEntry): number {
   return (
diff --git a/src/renderer/src/components/right-sidebar/source-control-tree.ts b/src/renderer/src/components/right-sidebar/source-control-tree.ts
index 6bf94893b07..2166b1489d2 100644
--- a/src/renderer/src/components/right-sidebar/source-control-tree.ts
+++ b/src/renderer/src/components/right-sidebar/source-control-tree.ts
@@ -1,5 +1,6 @@
 import { normalizeRelativePath } from '@/lib/path'
 import type { GitStatusEntry, GitStagingArea } from '../../../../shared/types'
+import { compareFileNames } from '../../../../shared/file-name-sort'
 import { splitPathSegments } from './path-tree'
 import { compareGitStatusEntries, sourceControlPathCollator } from './source-control-status-sort'
 
@@ -90,7 +91,9 @@ function finalizeDirectoryNode<Entry extends SourceControlTreeEntry, Area extend
     }
   }
 
-  directories.sort((a, b) => a.name.localeCompare(b.name))
+  // Why: keep directory ordering consistent with the numeric path collator used
+  // for the file rows one line below.
+  directories.sort((a, b) => compareFileNames(a.name, b.name))
   files.sort((a, b) => compareEntries(a.entry, b.entry))
   const fileCount =
     files.length + directories.reduce((count, directory) => count + directory.fileCount, 0)
diff --git a/src/shared/file-name-sort.test.ts b/src/shared/file-name-sort.test.ts
new file mode 100644
index 00000000000..85046075635
--- /dev/null
+++ b/src/shared/file-name-sort.test.ts
@@ -0,0 +1,38 @@
+import { describe, expect, it } from 'vitest'
+import { compareFileNames } from './file-name-sort'
+
+describe('compareFileNames', () => {
+  it('sorts numeric name segments naturally instead of lexicographically', () => {
+    const names = [
+      '1 - item.txt',
+      '100 - item.txt',
+      '2 - item.txt',
+      '200 - item.txt',
+      '409 - item.txt',
+      '41 - item.txt',
+      '410 - item.txt',
+      '9 - item.txt',
+      '99 - item.txt'
+    ]
+    expect([...names].sort(compareFileNames)).toEqual([
+      '1 - item.txt',
+      '2 - item.txt',
+      '9 - item.txt',
+      '41 - item.txt',
+      '99 - item.txt',
+      '100 - item.txt',
+      '200 - item.txt',
+      '409 - item.txt',
+      '410 - item.txt'
+    ])
+  })
+
+  it('sorts embedded numbers naturally within alphabetical order', () => {
+    expect(['b1.md', 'a10.md', 'a2.md', 'a1.md'].sort(compareFileNames)).toEqual([
+      'a1.md',
+      'a2.md',
+      'a10.md',
+      'b1.md'
+    ])
+  })
+})
diff --git a/src/shared/file-name-sort.ts b/src/shared/file-name-sort.ts
new file mode 100644
index 00000000000..3c1553440d7
--- /dev/null
+++ b/src/shared/file-name-sort.ts
@@ -0,0 +1,8 @@
+// Why hoisted: localeCompare with an options object resolves a fresh ICU collator
+// on every comparison, so a directory sort paid for one per O(n log n) step.
+// numeric: true orders "99 - a" before "100 - b", matching Finder/Explorer.
+export const fileNameCollator = new Intl.Collator(undefined, { numeric: true })
+
+export function compareFileNames(a: string, b: string): number {
+  return fileNameCollator.compare(a, b)
+}