diff --git a/src/lib/components/Editor.svelte b/src/lib/components/Editor.svelte
index dd0b886..94690f5 100644
--- a/src/lib/components/Editor.svelte
+++ b/src/lib/components/Editor.svelte
@@ -48,6 +48,7 @@
 	import { WrapSelectedText } from '$lib/editor/extensions/wrapSelectedText';
 	import { calloutGroup, calloutIcon, calloutLabel, CALLOUT_MENU, transformCalloutBlockquotes, serializeCallout } from '$lib/editor/callouts';
 	import { wrapTextareaSelection } from '$lib/editor/source/selectionPairs';
+	import { relativePath } from '$lib/utils/paths';
 	import GraphView from './GraphView.svelte';
 	import TagSuggestInput from './TagSuggestInput.svelte';
 	import { isMobile, isAndroid } from '$lib/platform';
@@ -3697,7 +3698,7 @@
 			}
 		}
 		// Convert asset:// URLs back to relative paths for saving
-		if (!src.startsWith('asset:') && !src.startsWith('http://asset.localhost')) return src;
+		if (!src.startsWith('asset:') && !src.startsWith('http://asset.localhost') && !src.startsWith('https://asset.localhost')) return src;
 		let absPath = '';
 		try {
 			const url = new URL(src);
@@ -3707,18 +3708,20 @@
 		}
 		// Clean up any leading double/triple slashes (URL parsing artifact)
 		absPath = absPath.replace(/^\/{2,}/, '/');
-		// Make relative to note directory (matches how resolveImageSrc works)
+		absPath = absPath.replace(/^\/([A-Za-z]:\/)/, '$1').replace(/\\/g, '/');
+		// Preserve note-relative paths, including parent-directory segments.
 		const notePath = $activeNotePath;
-		if (notePath) {
-			const noteDir = notePath.substring(0, notePath.lastIndexOf('/'));
-			if (absPath.startsWith(noteDir + '/')) {
-				return absPath.substring(noteDir.length + 1);
-			}
-		}
-		// Fallback: make relative to vault root
-		const vaultRoot = $appConfig?.active_vault;
+		const vaultRoot = $appConfig?.active_vault?.replace(/\\/g, '/').replace(/\/$/, '');
 		if (vaultRoot && absPath.startsWith(vaultRoot + '/')) {
-			return absPath.substring(vaultRoot.length + 1);
+			const vaultRelative = absPath.substring(vaultRoot.length + 1);
+			// HelixNotes-managed attachments have explicit vault-root semantics.
+			if (vaultRelative.startsWith('.helixnotes/')) return vaultRelative;
+			if (notePath) {
+				const normalizedNotePath = notePath.replace(/\\/g, '/');
+				const noteDir = normalizedNotePath.substring(0, normalizedNotePath.lastIndexOf('/'));
+				return relativePath(noteDir, absPath);
+			}
+			return vaultRelative;
 		}
 		return absPath;
 	}
diff --git a/src/lib/components/NoteList.svelte b/src/lib/components/NoteList.svelte
index 204c135..5430edd 100644
--- a/src/lib/components/NoteList.svelte
+++ b/src/lib/components/NoteList.svelte
@@ -787,6 +787,19 @@
 		}
 	}
 
+	function isFiled(note: NoteEntry): boolean {
+		const vaultRoot = $appConfig?.active_vault?.replace(/\\/g, '/').replace(/\/$/, '');
+		if (!vaultRoot) return false;
+		const normalizedPath = note.path.replace(/\\/g, '/');
+		const noteDir = normalizedPath.substring(0, normalizedPath.lastIndexOf('/'));
+		return noteDir !== vaultRoot;
+	}
+
+	function unfileNote(note: NoteEntry) {
+		const vaultRoot = $appConfig?.active_vault;
+		if (vaultRoot) handleMoveNote(note, vaultRoot);
+	}
+
 	function clampMenu(x: number, y: number, menuWidth = 220, menuHeight = 400): { x: number; y: number } {
 		if (x + menuWidth > window.innerWidth) x = window.innerWidth - menuWidth - 8;
 		if (y + menuHeight > window.innerHeight) y = window.innerHeight - menuHeight - 8;
@@ -1535,6 +1548,14 @@
 				</svg>
 				Move to...
 			</button>
+			{#if isFiled(contextMenu.note)}
+			<button onclick={() => unfileNote(contextMenu!.note)}>
+				<svg width="12" height="12" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round">
+					<path d="M22 19a2 2 0 01-2 2H4a2 2 0 01-2-2V5a2 2 0 012-2h5l2 3h9a2 2 0 012 2z"/><path d="M9 13h6"/>
+				</svg>
+				Unfile Note
+			</button>
+			{/if}
 			{#if !isMobile}
 			<button onclick={async () => { const n = contextMenu!.note; contextMenu = null; await selectNote(n); setTimeout(() => window.print(), 300); }}>
 				<svg width="12" height="12" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round">
diff --git a/src/lib/utils/paths.ts b/src/lib/utils/paths.ts
new file mode 100644
index 0000000..f12b7e2
--- /dev/null
+++ b/src/lib/utils/paths.ts
@@ -0,0 +1,28 @@
+function pathParts(path: string): string[] {
+	return path.replace(/\\/g, '/').split('/').filter(Boolean);
+}
+
+function pathRoot(path: string): string {
+	const normalized = path.replace(/\\/g, '/');
+	const drive = normalized.match(/^([A-Za-z]:)\//);
+	if (drive) return drive[1].toLowerCase();
+	return normalized.startsWith('/') ? '/' : '';
+}
+
+export function relativePath(fromDirectory: string, targetPath: string): string {
+	const from = pathParts(fromDirectory);
+	const target = pathParts(targetPath);
+	if (pathRoot(fromDirectory) !== pathRoot(targetPath)) return targetPath.replace(/\\/g, '/');
+	const windowsPath = /^[A-Za-z]:[\\/]/.test(fromDirectory) || /^[A-Za-z]:[\\/]/.test(targetPath);
+	const equal = windowsPath
+		? (left: string, right: string) => left.toLowerCase() === right.toLowerCase()
+		: (left: string, right: string) => left === right;
+
+	let common = 0;
+	while (common < from.length && common < target.length && equal(from[common], target[common])) {
+		common++;
+	}
+
+	const result = [...Array(from.length - common).fill('..'), ...target.slice(common)];
+	return result.join('/') || '.';
+}