diff --git a/pkg/agent/context.go b/pkg/agent/context.go
index fb03979e5..2692bc7a1 100644
--- a/pkg/agent/context.go
+++ b/pkg/agent/context.go
@@ -786,12 +786,31 @@ func (cb *ContextBuilder) MatchSkillsInMessage(message string) []string {
 }
 
 // LoadSkillContext loads the full SKILL.md content for the given skill names
-// via the underlying SkillsLoader.
+// via the underlying SkillsLoader. It resolves frontmatter names to directory
+// names so that skills whose metadata name differs from the directory name
+// are loaded correctly.
 func (cb *ContextBuilder) LoadSkillContext(skillNames []string) string {
-	if cb.skillsLoader == nil {
+	if cb.skillsLoader == nil || len(skillNames) == 0 {
 		return ""
 	}
-	return cb.skillsLoader.LoadSkillsForContext(skillNames)
+
+	allSkills := cb.skillsLoader.ListSkills()
+	nameToDir := make(map[string]string, len(allSkills))
+	for _, s := range allSkills {
+		dirName := filepath.Base(filepath.Dir(s.Path))
+		nameToDir[strings.ToLower(s.Name)] = dirName
+	}
+
+	resolved := make([]string, 0, len(skillNames))
+	for _, name := range skillNames {
+		if dir, ok := nameToDir[strings.ToLower(name)]; ok {
+			resolved = append(resolved, dir)
+		} else {
+			resolved = append(resolved, name)
+		}
+	}
+
+	return cb.skillsLoader.LoadSkillsForContext(resolved)
 }
 
 // isSkillNameChar returns true for characters that can appear inside a skill
diff --git a/pkg/agent/context_skills_test.go b/pkg/agent/context_skills_test.go
index c1c9edfd7..c187af459 100644
--- a/pkg/agent/context_skills_test.go
+++ b/pkg/agent/context_skills_test.go
@@ -171,6 +171,35 @@ func TestLoadSkillContext(t *testing.T) {
 	}
 }
 
+func TestLoadSkillContext_MetadataNameDiffersFromDir(t *testing.T) {
+	tmpDir := setupWorkspace(t, nil)
+	defer os.RemoveAll(tmpDir)
+
+	createTestSkill(
+		t,
+		filepath.Join(tmpDir, "skills"),
+		"weather-skill",
+		"weather",
+		"Get weather",
+		"Call the weather API (metadata name test).",
+	)
+
+	cb := NewContextBuilder(tmpDir)
+
+	matched := cb.MatchSkillsInMessage("use the weather skill")
+	if len(matched) == 0 {
+		t.Fatal("expected to match skill by metadata name 'weather'")
+	}
+
+	ctx := cb.LoadSkillContext(matched)
+	if ctx == "" {
+		t.Fatal("expected non-empty skill context when metadata name differs from directory name")
+	}
+	if !strings.Contains(ctx, "metadata name test") {
+		t.Errorf("skill context should contain skill body, got: %s", ctx)
+	}
+}
+
 func TestLoadSkillContext_NilLoader(t *testing.T) {
 	cb := &ContextBuilder{skillsLoader: nil}
 	ctx := cb.LoadSkillContext([]string{"weather"})
diff --git a/pkg/agent/loop.go b/pkg/agent/loop.go
index 8da52d6a6..1a9a5d48a 100644
--- a/pkg/agent/loop.go
+++ b/pkg/agent/loop.go
@@ -61,6 +61,7 @@ type processOptions struct {
 	EnableSummary   bool     // Whether to trigger summarization
 	SendResponse    bool     // Whether to send response via bus
 	NoHistory       bool     // If true, don't load session history (for heartbeat)
+	SkillContext    string   // Injected SKILL.md content for matched skills
 }
 
 const (
@@ -802,11 +803,10 @@ func (al *AgentLoop) runAgentLoop(
 	}
 
 	// Auto-inject SKILL.md content when the user references an installed skill.
-	var skillCtx string
 	if matched := agent.ContextBuilder.MatchSkillsInMessage(opts.UserMessage); len(matched) > 0 {
-		skillCtx = agent.ContextBuilder.LoadSkillContext(matched)
+		opts.SkillContext = agent.ContextBuilder.LoadSkillContext(matched)
 		logger.DebugCF("agent", "Skills matched in user message",
-			map[string]any{"matched": matched, "context_len": len(skillCtx)})
+			map[string]any{"matched": matched, "context_len": len(opts.SkillContext)})
 	}
 
 	messages := agent.ContextBuilder.BuildMessages(
@@ -816,7 +816,7 @@ func (al *AgentLoop) runAgentLoop(
 		opts.Media,
 		opts.Channel,
 		opts.ChatID,
-		skillCtx,
+		opts.SkillContext,
 	)
 
 	// Resolve media:// refs to base64 data URLs (streaming)
@@ -1085,6 +1085,7 @@ func (al *AgentLoop) runLLMIteration(
 				messages = agent.ContextBuilder.BuildMessages(
 					newHistory, newSummary, "",
 					nil, opts.Channel, opts.ChatID,
+					opts.SkillContext,
 				)
 				continue
 			}