diff --git a/server/src/__tests__/company-skills.test.ts b/server/src/__tests__/company-skills.test.ts
index 17da78042..bcc173d8b 100644
--- a/server/src/__tests__/company-skills.test.ts
+++ b/server/src/__tests__/company-skills.test.ts
@@ -5,6 +5,7 @@ import { afterEach, describe, expect, it } from "vitest";
 import {
   discoverProjectWorkspaceSkillDirectories,
   findMissingLocalSkillIds,
+  normalizeGitHubSkillDirectory,
   parseSkillImportSourceInput,
   readLocalSkillImportFromDirectory,
 } from "../services/company-skills.js";
@@ -86,6 +87,13 @@ describe("company skill import source parsing", () => {
 });
 
 describe("project workspace skill discovery", () => {
+  it("normalizes GitHub skill directories for blob imports and legacy metadata", () => {
+    expect(normalizeGitHubSkillDirectory("retro/.", "retro")).toBe("retro");
+    expect(normalizeGitHubSkillDirectory("retro/SKILL.md", "retro")).toBe("retro");
+    expect(normalizeGitHubSkillDirectory("SKILL.md", "root-skill")).toBe("");
+    expect(normalizeGitHubSkillDirectory("", "fallback-skill")).toBe("fallback-skill");
+  });
+
   it("finds bounded skill roots under supported workspace paths", async () => {
     const workspace = await makeTempDir("paperclip-skill-workspace-");
     await writeSkillDir(workspace, "Workspace Root");
diff --git a/server/src/services/company-skills.ts b/server/src/services/company-skills.ts
index 43de8ee6b..2b97da208 100644
--- a/server/src/services/company-skills.ts
+++ b/server/src/services/company-skills.ts
@@ -190,6 +190,18 @@ function normalizeSkillKey(value: string | null | undefined) {
   return segments.length > 0 ? segments.join("/") : null;
 }
 
+export function normalizeGitHubSkillDirectory(
+  value: string | null | undefined,
+  fallback: string,
+) {
+  const normalized = normalizePortablePath(value ?? "");
+  if (!normalized) return normalizePortablePath(fallback);
+  if (path.posix.basename(normalized).toLowerCase() === "skill.md") {
+    return normalizePortablePath(path.posix.dirname(normalized));
+  }
+  return normalized;
+}
+
 function hashSkillValue(value: string) {
   return createHash("sha256").update(value).digest("hex").slice(0, 10);
 }
@@ -1019,7 +1031,10 @@ async function readUrlSkillImports(
         repo: parsed.repo,
         ref: ref,
         trackingRef,
-        repoSkillDir: basePrefix ? `${basePrefix}${skillDir}` : skillDir,
+        repoSkillDir: normalizeGitHubSkillDirectory(
+          basePrefix ? `${basePrefix}${skillDir}` : skillDir,
+          slug,
+        ),
       };
       const inventory = filteredPaths
         .filter((entry) => entry === relativeSkillPath || entry.startsWith(`${skillDir}/`))
@@ -1665,7 +1680,7 @@ export function companySkillService(db: Db) {
       const owner = asString(metadata.owner);
       const repo = asString(metadata.repo);
       const ref = skill.sourceRef ?? asString(metadata.ref) ?? "main";
-      const repoSkillDir = normalizePortablePath(asString(metadata.repoSkillDir) ?? skill.slug);
+      const repoSkillDir = normalizeGitHubSkillDirectory(asString(metadata.repoSkillDir), skill.slug);
       if (!owner || !repo) {
         throw unprocessable("Skill source metadata is incomplete.");
       }