diff --git a/CHANGELOG.md b/CHANGELOG.md
index 0264025..fca05aa 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,15 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ## [Unreleased]
 
+### Fixed
+
+- The check that keeps saved images inside the workspace now follows links in
+  the part of the path that already exists when the folders below it do not
+  exist yet. A save directory whose existing part was a link leading out of the
+  workspace, followed by folders still to be created, passed the check, so the
+  folders and the image were created on the far side of the link. The same gap
+  refused new nested folders in a workspace opened through a link.
+
 ## [0.9.0] - 2026-09-18
 
 **Breaking: VS Code 1.138 or later is now required**, up from 1.137, in step with
diff --git a/src/security/path-validator.ts b/src/security/path-validator.ts
index a039d20..ea23a20 100644
--- a/src/security/path-validator.ts
+++ b/src/security/path-validator.ts
@@ -28,24 +28,8 @@ export async function validatePathInsideWorkspace(
     // Normalize both paths
     const normalizedWorkspace = normalizePath(realWorkspaceRoot);
 
-    // Check if target path exists
-    let realTargetPath: string;
-    try {
-      // If target exists, resolve its real path
-      realTargetPath = await fs.realpath(targetPath);
-    } catch {
-      // Target doesn't exist yet - validate parent directory
-      const parentDir = path.dirname(targetPath);
-      try {
-        const realParentDir = await fs.realpath(parentDir);
-        realTargetPath = path.join(realParentDir, path.basename(targetPath));
-      } catch {
-        // Parent doesn't exist - check the constructed path
-        // This is acceptable for new directories that will be created
-        const resolvedTarget = path.resolve(workspaceRoot, targetPath);
-        realTargetPath = resolvedTarget;
-      }
-    }
+    // Resolve the target through links as far as it exists
+    const realTargetPath = await resolveExistingPrefix(targetPath, workspaceRoot);
 
     const normalizedTarget = normalizePath(realTargetPath);
 
@@ -72,6 +56,41 @@ export async function validatePathInsideWorkspace(
   }
 }
 
+/**
+ * Resolve a path through links as far as it exists, then append the rest.
+ *
+ * `realpath` fails on a path that does not exist yet, so the nearest ancestor
+ * that does exist is resolved instead and the missing segments are appended to
+ * it. Resolving less than that — only the parent, or nothing once the parent is
+ * missing too — lets a link in the existing part lead out of the workspace
+ * unseen, while a workspace that is itself reached through a link stops looking
+ * like it contains its own new folders.
+ *
+ * @param targetPath - The path to resolve; a relative path is taken from the workspace root
+ * @param workspaceRoot - The workspace root path
+ * @returns The real path of the existing part, followed by the missing segments
+ */
+async function resolveExistingPrefix(targetPath: string, workspaceRoot: string): Promise<string> {
+  const absolute = path.isAbsolute(targetPath) ? targetPath : path.join(workspaceRoot, targetPath);
+  const missing: string[] = [];
+  let current = absolute;
+
+  for (;;) {
+    try {
+      const real = await fs.realpath(current);
+      return path.join(real, ...missing.reverse());
+    } catch {
+      const parent = path.dirname(current);
+      if (parent === current) {
+        // Not even the root resolved: compare the path as given
+        return path.resolve(absolute);
+      }
+      missing.push(path.basename(current));
+      current = parent;
+    }
+  }
+}
+
 /**
  * Check if a path contains parent directory traversal (..)
  *
diff --git a/test/security/path-validator-workspace.test.ts b/test/security/path-validator-workspace.test.ts
new file mode 100644
index 0000000..2d80595
--- /dev/null
+++ b/test/security/path-validator-workspace.test.ts
@@ -0,0 +1,100 @@
+import * as fs from 'fs/promises';
+import * as os from 'os';
+import * as path from 'path';
+import { afterAll, beforeAll, describe, expect, it } from 'vitest';
+import { PathValidationError } from '../../src/core/errors';
+import { validatePathInsideWorkspace } from '../../src/security/path-validator';
+
+// A real directory tree rather than mocks: what this function exists for — a
+// link that leads out of the workspace — only shows up on a real file system.
+// Directory links are junctions, which Windows creates without privileges;
+// elsewhere the type argument is ignored.
+describe('validatePathInsideWorkspace', () => {
+  let root: string;
+  let workspace: string;
+  let outside: string;
+  let linkOut: string;
+  let linkedWorkspace: string;
+
+  beforeAll(async () => {
+    root = await fs.mkdtemp(path.join(os.tmpdir(), 'clipshot-containment-'));
+    workspace = path.join(root, 'workspace');
+    outside = path.join(root, 'outside');
+    await fs.mkdir(path.join(workspace, 'images'), { recursive: true });
+    await fs.mkdir(outside);
+    await fs.writeFile(path.join(workspace, 'images', 'inside.png'), '');
+    await fs.writeFile(path.join(outside, 'secret.txt'), '');
+
+    linkOut = path.join(workspace, 'link-out');
+    await fs.symlink(outside, linkOut, 'junction');
+
+    linkedWorkspace = path.join(root, 'workspace-link');
+    await fs.symlink(workspace, linkedWorkspace, 'junction');
+  });
+
+  afterAll(async () => {
+    await fs.rm(root, { recursive: true, force: true });
+  });
+
+  describe('inside the workspace', () => {
+    it('accepts an existing file', async () => {
+      await expect(
+        validatePathInsideWorkspace(path.join(workspace, 'images', 'inside.png'), workspace)
+      ).resolves.toBe(true);
+    });
+
+    it('accepts a file that does not exist yet in an existing folder', async () => {
+      await expect(
+        validatePathInsideWorkspace(path.join(workspace, 'images', 'new.png'), workspace)
+      ).resolves.toBe(true);
+    });
+
+    it('accepts folders that do not exist yet, several levels deep', async () => {
+      await expect(
+        validatePathInsideWorkspace(path.join(workspace, 'new', 'deeper', 'image.png'), workspace)
+      ).resolves.toBe(true);
+    });
+
+    // A workspace opened through a link (a symlinked home directory, macOS's
+    // /var, an 8.3 short name on Windows) resolves to a different string than
+    // the path the caller builds from it. The check has to compare real paths
+    // on both sides, including for folders that do not exist yet.
+    it('accepts new folders under a workspace that is itself reached through a link', async () => {
+      await expect(
+        validatePathInsideWorkspace(
+          path.join(linkedWorkspace, 'new', 'deeper', 'image.png'),
+          linkedWorkspace
+        )
+      ).resolves.toBe(true);
+    });
+  });
+
+  describe('outside the workspace', () => {
+    it('rejects an absolute path outside', async () => {
+      await expect(
+        validatePathInsideWorkspace(path.join(outside, 'secret.txt'), workspace)
+      ).rejects.toBeInstanceOf(PathValidationError);
+    });
+
+    it('rejects an existing file reached through a link that leads outside', async () => {
+      await expect(
+        validatePathInsideWorkspace(path.join(linkOut, 'secret.txt'), workspace)
+      ).rejects.toBeInstanceOf(PathValidationError);
+    });
+
+    it('rejects a new file directly under a link that leads outside', async () => {
+      await expect(
+        validatePathInsideWorkspace(path.join(linkOut, 'new.png'), workspace)
+      ).rejects.toBeInstanceOf(PathValidationError);
+    });
+
+    // The case the folder-creating callers reach: `writeAtomic` and `ensureDir`
+    // validate first and then `mkdir -p`, so accepting this would create the
+    // folders — and write the image — on the far side of the link.
+    it('rejects new folders under a link that leads outside', async () => {
+      await expect(
+        validatePathInsideWorkspace(path.join(linkOut, 'new', 'deeper', 'image.png'), workspace)
+      ).rejects.toBeInstanceOf(PathValidationError);
+    });
+  });
+});