diff --git a/Cargo.lock b/Cargo.lock
index 1118dea..379d37f 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -78,6 +78,11 @@ dependencies = [
  "subtle",
 ]
 
+[[package]]
+name = "agent-skills"
+version = "0.1.0"
+source = "git+https://github.com/datadog-labs/agent-skills?rev=6d3e516b7072bd1470563a5d10e941e2cad58ebe#6d3e516b7072bd1470563a5d10e941e2cad58ebe"
+
 [[package]]
 name = "aho-corasick"
 version = "1.1.4"
@@ -2729,6 +2734,7 @@ name = "pup"
 version = "0.65.3"
 dependencies = [
  "aes-gcm 0.10.3",
+ "agent-skills",
  "anyhow",
  "async-trait",
  "base64 0.22.1",
diff --git a/Cargo.toml b/Cargo.toml
index ed18a37..d1ab50f 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -68,6 +68,12 @@ browser = [
 ]
 
 [dependencies]
+# Skills content from datadog-labs/agent-skills, consumed as a Cargo git dep.
+# Pinned to a specific rev so updates are explicit and auditable, matching
+# the same pattern used for datadog-api-client below.
+# Requires agent-skills to carry a Cargo.toml + src/lib.rs (see companion PR).
+agent-skills = { git = "https://github.com/datadog-labs/agent-skills", rev = "6d3e516b7072bd1470563a5d10e941e2cad58ebe" }
+
 # CLI (optional — not needed for browser WASM library)
 clap = { version = "4", features = ["derive"], optional = true }
 clap_complete = { version = "4", optional = true }
diff --git a/src/commands/skills.rs b/src/commands/skills.rs
index c7b2b3b..2e3ba7c 100644
--- a/src/commands/skills.rs
+++ b/src/commands/skills.rs
@@ -293,6 +293,33 @@ mod tests {
     use super::*;
     use crate::config::Config;
     use crate::test_support::TempDir;
+    use agent_skills;
+
+    fn count_files_recursive(dir: &std::path::Path) -> usize {
+        std::fs::read_dir(dir)
+            .unwrap_or_else(|e| {
+                panic!(
+                    "count_files_recursive: failed to read '{}': {e}",
+                    dir.display()
+                )
+            })
+            .map(|e| {
+                let p = e
+                    .unwrap_or_else(|err| {
+                        panic!(
+                            "count_files_recursive: entry error in '{}': {err}",
+                            dir.display()
+                        )
+                    })
+                    .path();
+                if p.is_dir() {
+                    count_files_recursive(&p)
+                } else {
+                    1
+                }
+            })
+            .sum()
+    }
 
     fn base_cfg() -> Config {
         Config {
@@ -463,19 +490,30 @@ mod tests {
             "dd-pup-pi extension should be installed when `all` is selected"
         );
         assert!(tmp.path().join("dd-pup-pi/package.json").exists());
-        // With path dedup, --dir writes each unique destination exactly once:
-        // dd-apm/SKILL.md + dd-pup-pi/index.ts + dd-pup-pi/package.json + dd-pup-pi/README.md
-        let file_count = std::fs::read_dir(tmp.path())
-            .unwrap()
-            .flat_map(|d| {
-                std::fs::read_dir(d.unwrap().path())
-                    .unwrap()
-                    .map(|f| f.unwrap().path())
-            })
-            .count();
-        assert_eq!(
-            file_count, 4,
-            "expected 4 unique files (1 skill + 3 extension)"
+        assert!(tmp.path().join("dd-pup-pi/README.md").exists());
+        assert!(
+            tmp.path()
+                .join("dd-apm/k8s-ssi/agent-install/SKILL.md")
+                .exists(),
+            "k8s-ssi sub-skill nested path must be preserved"
+        );
+        assert!(
+            tmp.path()
+                .join("dd-apm/linux-ssi/agent-install/SKILL.md")
+                .exists(),
+            "linux-ssi sub-skill nested path must be preserved"
+        );
+        // Guard against silent mass-install failure: floor is derived from the
+        // crate's own constants so it grows automatically as sub-skills are added.
+        let ext_files = 3usize; // dd-pup-pi: index.ts + package.json + README.md
+        let apm_min = 1 + agent_skills::DD_APM_SUB_SKILLS.len(); // root + sub-skills
+        let file_count = count_files_recursive(tmp.path());
+        assert!(
+            file_count >= ext_files + apm_min,
+            "expected at least {exp} files (1+{subs} apm + {ext} ext), got {file_count}",
+            exp = ext_files + apm_min,
+            subs = agent_skills::DD_APM_SUB_SKILLS.len(),
+            ext = ext_files,
         );
     }
 
diff --git a/src/skills.rs b/src/skills.rs
index a3049e7..81aab99 100644
--- a/src/skills.rs
+++ b/src/skills.rs
@@ -12,9 +12,14 @@ pub struct SkillEntry {
     /// Platform slug for entry_type == "extension". One of: "pi".
     /// Empty for skills and agents.
     pub platform: &'static str,
-    /// Files to materialize for entry_type == "extension".
-    /// Each tuple is `(relative_path_within_extension_dir, file_contents)`.
-    /// Empty for skills and agents.
+    /// Extra files to materialize alongside the entry.
+    /// Each tuple is `(relative_path, file_contents)`, written verbatim.
+    /// - For `extension`: relative to the extension's install dir; this is
+    ///   the only source of files (`content` is empty).
+    /// - For `skill`: relative to the parent skill's install dir, used to
+    ///   ship nested sub-skill SKILL.md files (e.g. `dd-apm` ships
+    ///   `service-remapping/SKILL.md` and the k8s-ssi/linux-ssi trees).
+    /// - For `agent`: unused; leave empty.
     pub files: &'static [(&'static str, &'static str)],
 }
 
@@ -64,9 +69,9 @@ pub static SKILLS: &[SkillEntry] = &[
         name: "dd-apm",
         description: "APM - traces, services, dependencies, performance analysis.",
         entry_type: "skill",
-        content: include_str!("../skills/dd-apm/SKILL.md"),
+        content: agent_skills::DD_APM_SKILL,
         platform: "",
-        files: &[],
+        files: agent_skills::DD_APM_SUB_SKILLS,
     },
     SkillEntry {
         name: "dd-debugger",
@@ -928,7 +933,19 @@ pub fn install_paths(
     else {
         return Ok(vec![]);
     };
-    Ok(vec![(path, format_content(entry, &fmt))])
+    let mut out = vec![(path.clone(), format_content(entry, &fmt))];
+    // Skills can ship nested sub-skill files alongside the root SKILL.md
+    // (e.g. dd-apm's k8s-ssi/, linux-ssi/, service-remapping/ trees).
+    // Only applies when the parent installs as a skill directory; subagent
+    // .md files have no surrounding directory to nest under.
+    if fmt == InstallFormat::SkillMd && !entry.files.is_empty() {
+        if let Some(parent_dir) = path.parent() {
+            for (rel, body) in entry.files {
+                out.push((parent_dir.join(rel), (*body).to_string()));
+            }
+        }
+    }
+    Ok(out)
 }
 
 #[derive(Debug, PartialEq)]
@@ -1501,6 +1518,48 @@ mod tests {
         assert_eq!(extensions_dir("claude-code", &root, false), None);
     }
 
+    #[test]
+    fn test_install_paths_skill_with_sub_skills() {
+        static SUB_FILES: &[(&str, &str)] = &[
+            ("service-remapping/SKILL.md", "# Service Remapping"),
+            ("k8s-ssi/agent-install/SKILL.md", "# K8s Agent Install"),
+        ];
+        let root = PathBuf::from("/tmp/proj");
+        let e = SkillEntry {
+            files: SUB_FILES,
+            ..entry("dd-apm", "skill", "body")
+        };
+        let paths = install_paths(&e, "claude-code", &root, None, false).unwrap();
+        assert_eq!(paths.len(), 3);
+        assert_eq!(paths[0].0, root.join(".claude/skills/dd-apm/SKILL.md"));
+        assert_eq!(
+            paths[1].0,
+            root.join(".claude/skills/dd-apm/service-remapping/SKILL.md")
+        );
+        assert_eq!(
+            paths[2].0,
+            root.join(".claude/skills/dd-apm/k8s-ssi/agent-install/SKILL.md")
+        );
+    }
+
+    #[test]
+    fn test_install_paths_sub_skills_skipped_for_agent_md() {
+        // AgentMd format (Claude Code agents dir) has no surrounding directory,
+        // so sub-skill files must not be written.
+        static SUB_FILES: &[(&str, &str)] = &[("sub/SKILL.md", "# Sub")];
+        let root = PathBuf::from("/tmp/proj");
+        let e = SkillEntry {
+            files: SUB_FILES,
+            ..entry("dd-apm", "agent", "body")
+        };
+        let paths = install_paths(&e, "claude-code", &root, None, false).unwrap();
+        assert_eq!(
+            paths.len(),
+            1,
+            "sub-skills must not be written for agent-md format"
+        );
+    }
+
     #[test]
     fn test_install_paths_skill_single_file() {
         let root = PathBuf::from("/tmp/proj");