diff --git a/docs/guide/separate-input-root.md b/docs/guide/separate-input-root.md
index 0492890eb..aa0c1a501 100644
--- a/docs/guide/separate-input-root.md
+++ b/docs/guide/separate-input-root.md
@@ -55,4 +55,4 @@ rulesync generate --input-root ~/.aiglobal --global --targets claudecode --featu
 
 Rulesync follows symbolic links during file discovery. A symlink inside `.rulesync/` that points outside the directory will be followed transparently, and the resolved file content will be copied into the generated output. This is intentional: it lets you centralize shared skills or rules in one place and reference them via symlinks from multiple project directories without duplication.
 
-The trust boundary is the directory you point Rulesync at. `--input-root` is `resolve()`-ed to an absolute path before use, but there is no `realpath`-based boundary check on individual symlinks inside it. Only run Rulesync against trees you control.
+The trust boundary is the directory you point Rulesync at. `--input-root` is `resolve()`-ed to an absolute path before use, but there is no `realpath`-based boundary check on individual symlinks inside it. Only run Rulesync against trees you control. Directory symlink cycles are handled safely — discovery results are deduplicated by real path, so a cycle does not produce duplicated output. See the [File Formats § Symlinks](../reference/file-formats.md#symlinks) note for the behavior that applies across all features.
diff --git a/docs/reference/file-formats.md b/docs/reference/file-formats.md
index 6d4cfccc4..a99caea68 100644
--- a/docs/reference/file-formats.md
+++ b/docs/reference/file-formats.md
@@ -1,5 +1,11 @@
 # File Formats
 
+## Symlinks
+
+Rulesync follows symbolic links when it discovers source files, whether you use a plain `.rulesync/` directory or a separate `--input-root`. Glob-based discovery (rules, commands, subagents, skills) follows symlinked files and directories; single fixed-path files such as `.rulesyncignore`, `.rulesync/mcp.json`, and `.rulesync/permissions.json` are likewise resolved transparently by the OS when read. A symlink inside the input tree that points elsewhere is followed transparently, and the resolved file content is copied into the generated output. This is intentional: it lets you centralize shared skills or rules in one place and reference them via symlinks without duplication (see [issue #1707](https://github.com/dyoshikawa/rulesync/issues/1707)).
+
+The trust boundary is the directory you point Rulesync at. There is **no** `realpath`-based containment check on individual symlinks, so a link may resolve to a target outside the input root — enforcing containment would break the shared-file use case above. Only run Rulesync against trees you control. Directory symlink **cycles** are handled safely: results are deduplicated by real path, so a cycle does not produce duplicated output. Note that the remote-fetch path (`rulesync fetch` from a Git repository) is a separate, hardened code path that **skips** symlinks entirely, so untrusted remote content never has its symlinks followed.
+
 ## `rulesync/rules/*.md`
 
 Example:
diff --git a/skills/rulesync/file-formats.md b/skills/rulesync/file-formats.md
index 6d4cfccc4..a99caea68 100644
--- a/skills/rulesync/file-formats.md
+++ b/skills/rulesync/file-formats.md
@@ -1,5 +1,11 @@
 # File Formats
 
+## Symlinks
+
+Rulesync follows symbolic links when it discovers source files, whether you use a plain `.rulesync/` directory or a separate `--input-root`. Glob-based discovery (rules, commands, subagents, skills) follows symlinked files and directories; single fixed-path files such as `.rulesyncignore`, `.rulesync/mcp.json`, and `.rulesync/permissions.json` are likewise resolved transparently by the OS when read. A symlink inside the input tree that points elsewhere is followed transparently, and the resolved file content is copied into the generated output. This is intentional: it lets you centralize shared skills or rules in one place and reference them via symlinks without duplication (see [issue #1707](https://github.com/dyoshikawa/rulesync/issues/1707)).
+
+The trust boundary is the directory you point Rulesync at. There is **no** `realpath`-based containment check on individual symlinks, so a link may resolve to a target outside the input root — enforcing containment would break the shared-file use case above. Only run Rulesync against trees you control. Directory symlink **cycles** are handled safely: results are deduplicated by real path, so a cycle does not produce duplicated output. Note that the remote-fetch path (`rulesync fetch` from a Git repository) is a separate, hardened code path that **skips** symlinks entirely, so untrusted remote content never has its symlinks followed.
+
 ## `rulesync/rules/*.md`
 
 Example:
diff --git a/skills/rulesync/separate-input-root.md b/skills/rulesync/separate-input-root.md
index 0492890eb..aa0c1a501 100644
--- a/skills/rulesync/separate-input-root.md
+++ b/skills/rulesync/separate-input-root.md
@@ -55,4 +55,4 @@ rulesync generate --input-root ~/.aiglobal --global --targets claudecode --featu
 
 Rulesync follows symbolic links during file discovery. A symlink inside `.rulesync/` that points outside the directory will be followed transparently, and the resolved file content will be copied into the generated output. This is intentional: it lets you centralize shared skills or rules in one place and reference them via symlinks from multiple project directories without duplication.
 
-The trust boundary is the directory you point Rulesync at. `--input-root` is `resolve()`-ed to an absolute path before use, but there is no `realpath`-based boundary check on individual symlinks inside it. Only run Rulesync against trees you control.
+The trust boundary is the directory you point Rulesync at. `--input-root` is `resolve()`-ed to an absolute path before use, but there is no `realpath`-based boundary check on individual symlinks inside it. Only run Rulesync against trees you control. Directory symlink cycles are handled safely — discovery results are deduplicated by real path, so a cycle does not produce duplicated output. See the [File Formats § Symlinks](../reference/file-formats.md#symlinks) note for the behavior that applies across all features.
diff --git a/src/features/skills/skills-processor.test.ts b/src/features/skills/skills-processor.test.ts
index 1d550308b..fca1ef4be 100644
--- a/src/features/skills/skills-processor.test.ts
+++ b/src/features/skills/skills-processor.test.ts
@@ -1,3 +1,4 @@
+import { symlink } from "node:fs/promises";
 import { join } from "node:path";
 
 import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
@@ -424,6 +425,38 @@ Invalid content`;
       await expect(processor.loadRulesyncDirs()).rejects.toThrow();
     });
 
+    // End-to-end coverage for issue #1707: a skill directory under .rulesync/skills/ that is
+    // a symlink to a real directory elsewhere must be loaded like a regular skill. fs.symlink
+    // needs admin/Developer Mode on Windows, so this is skipped there (issue #1808 #5).
+    it.skipIf(process.platform === "win32")(
+      "should load a skill directory that is a symbolic link",
+      async () => {
+        const skillsDir = join(testDir, RULESYNC_SKILLS_RELATIVE_DIR_PATH);
+        await ensureDir(skillsDir);
+
+        // The real skill lives outside .rulesync/skills/, shared via a symlink.
+        const sharedSkillDir = join(testDir, "shared", "linked-skill");
+        await ensureDir(sharedSkillDir);
+        await writeFileContent(
+          join(sharedSkillDir, "SKILL.md"),
+          `---
+name: linked-skill
+description: Skill shared via a symbolic link
+---
+Linked skill content`,
+        );
+
+        await symlink(sharedSkillDir, join(skillsDir, "linked-skill"));
+
+        const rulesyncDirs = await processor.loadRulesyncDirs();
+
+        expect(rulesyncDirs).toHaveLength(1);
+        const rulesyncSkill = rulesyncDirs[0] as RulesyncSkill;
+        expect(rulesyncSkill.getFrontmatter().name).toBe("linked-skill");
+        expect(rulesyncSkill.getFrontmatter().description).toBe("Skill shared via a symbolic link");
+      },
+    );
+
     it("should throw error when directory without SKILL.md file is found", async () => {
       const skillsDir = join(testDir, RULESYNC_SKILLS_RELATIVE_DIR_PATH);
       await ensureDir(skillsDir);
diff --git a/src/utils/file.test.ts b/src/utils/file.test.ts
index db606f36b..de3c4e264 100644
--- a/src/utils/file.test.ts
+++ b/src/utils/file.test.ts
@@ -1,4 +1,4 @@
-import { symlink } from "node:fs/promises";
+import { realpath, symlink } from "node:fs/promises";
 import { join, resolve } from "node:path";
 
 import { afterEach, beforeEach, describe, expect, it } from "vitest";
@@ -551,7 +551,9 @@ describe("file utilities", () => {
         });
       });
 
-      describe("symlink support", () => {
+      // fs.symlink with the default/file type needs admin or Developer Mode on Windows, so
+      // these tests are skipped there (CI unit tests run on ubuntu). See issue #1808 #5.
+      describe.skipIf(process.platform === "win32")("symlink support", () => {
         it("should include a symlinked file in results", async () => {
           const realFile = join(testDir, "real.md");
           const linkedFile = join(testDir, "linked.md");
@@ -581,6 +583,40 @@ describe("file utilities", () => {
           });
           expect(fileResults).toContain(join(linkedDir, "SKILL.md"));
         });
+
+        it("should not produce duplicated entries when a directory symlink cycle exists", async () => {
+          // skills/a contains a real file and a link back to skills/, forming a cycle that
+          // globby follows up to the kernel ELOOP limit. Deduplication by real path collapses it.
+          const skillsDir = join(testDir, "skills");
+          const skillA = join(skillsDir, "a");
+          await ensureDir(skillA);
+          await writeFileContent(join(skillA, "SKILL.md"), "skill content");
+          await symlink(skillsDir, join(skillA, "loop"));
+
+          const fileResults = await findFilesByGlobs(join(skillsDir, "**", "*.md"), {
+            type: "file",
+          });
+
+          // Exactly one entry survives per real file despite the cycle (no ~40x blowup).
+          const uniqueRealPaths = new Set(await Promise.all(fileResults.map((p) => realpath(p))));
+          expect(uniqueRealPaths.size).toBe(fileResults.length);
+          expect(fileResults.length).toBeLessThan(5);
+        });
+
+        it("should keep only one path per real file when a link and its target both match", async () => {
+          const realFile = join(testDir, "real.md");
+          const linkedFile = join(testDir, "linked.md");
+          await writeFileContent(realFile, "content");
+          await symlink(realFile, linkedFile);
+
+          const results = await findFilesByGlobs(join(testDir, "*.md"), { type: "file" });
+
+          const realPaths = await Promise.all(results.map((p) => realpath(p)));
+          expect(new Set(realPaths).size).toBe(results.length);
+          // The sorted-first path (linked.md < real.md) survives; its target is dropped.
+          expect(results).toContain(linkedFile);
+          expect(results).not.toContain(realFile);
+        });
       });
     });
   });
diff --git a/src/utils/file.ts b/src/utils/file.ts
index 22e6164a8..218f1e0e0 100644
--- a/src/utils/file.ts
+++ b/src/utils/file.ts
@@ -1,4 +1,14 @@
-import { lstat, mkdir, mkdtemp, readdir, readFile, rm, stat, writeFile } from "node:fs/promises";
+import {
+  lstat,
+  mkdir,
+  mkdtemp,
+  readdir,
+  readFile,
+  realpath,
+  rm,
+  stat,
+  writeFile,
+} from "node:fs/promises";
 import os from "node:os";
 import { dirname, isAbsolute, join, relative, resolve } from "node:path";
 
@@ -220,18 +230,40 @@ export async function findFilesByGlobs(
     ? globs.map((g) => g.replaceAll("\\", "/"))
     : globs.replaceAll("\\", "/");
   // followSymbolicLinks: true lets callers use symlinks to share skills/rules across
-  // directories without duplication. Callers are responsible for passing globs rooted
-  // inside a trusted directory (inputRoot/outputRoot); this function has no path-boundary
-  // enforcement. Note: git-client.ts intentionally skips symlinks during remote fetch
-  // because unresolved symlinks in a bare clone are meaningless — that is a distinct code
-  // path with different trust assumptions.
+  // directories without duplication (see issue #1707). Callers operate on user-specified
+  // local trees that are inside the trust boundary, so symlinks are honored — including
+  // ones whose targets resolve outside the glob root. This is an intentional trade-off:
+  // enforcing realpath containment against a single root would break the #1707 use case of
+  // sharing files that live elsewhere in the same repository. Untrusted remote content is a
+  // separate code path: git-client.ts (`walkDirectory`) skips symlinks entirely as a
+  // security hardening for fetched repositories (commit 51bf0443), so this relaxed handling
+  // never applies to remote input.
   const results = globbySync(normalizedGlobs, {
     absolute: true,
     followSymbolicLinks: true,
     ...globbyOptions,
   });
-  // Sort for consistent ordering across different glob implementations
-  return results.toSorted();
+  // Deduplicate by real path so that directory symlink cycles (which globby follows up to
+  // the kernel ELOOP limit, ~40 levels) do not yield ~40x duplicated entries that would be
+  // read and re-emitted. Keep the first path per real file in sorted order for determinism.
+  const seenRealPaths = new Set<string>();
+  const deduped: string[] = [];
+  for (const result of results.toSorted()) {
+    let realResult: string;
+    try {
+      realResult = await realpath(result);
+    } catch {
+      // realpath can fail on a broken link or race; fall back to the literal path so the
+      // entry is still considered (and still deduplicated against identical literals).
+      realResult = result;
+    }
+    if (seenRealPaths.has(realResult)) {
+      continue;
+    }
+    seenRealPaths.add(realResult);
+    deduped.push(result);
+  }
+  return deduped;
 }
 
 export async function findRuleFiles(aiRulesDir: string): Promise<string[]> {