diff --git a/internal/cmdpolicy/engine.go b/internal/cmdpolicy/engine.go
index d46a39bcd..c2e7e0162 100644
--- a/internal/cmdpolicy/engine.go
+++ b/internal/cmdpolicy/engine.go
@@ -121,16 +121,16 @@ func (e *Engine) EvaluateOne(cmd *cobra.Command) Decision {
 		return Decision{
 			Allowed:    false,
 			ReasonCode: "risk_not_annotated",
-			Reason:     "command has no risk_level annotation; required when a Rule is active (set rule.allow_unannotated=true to opt out during gradual adoption)",
+			Reason:     "command has no risk_level annotation; rule denies unannotated commands",
 		}
 	}
 
 	// Axis 1: Deny has priority.
-	if matchesAny(r.Deny, path) {
+	if matched, ok := firstMatch(r.Deny, path); ok {
 		return Decision{
 			Allowed:    false,
 			ReasonCode: "command_denylisted",
-			Reason:     "command denied by rule deny list",
+			Reason:     fmt.Sprintf("command path %q matched deny pattern %q", path, matched),
 		}
 	}
 
@@ -139,7 +139,7 @@ func (e *Engine) EvaluateOne(cmd *cobra.Command) Decision {
 		return Decision{
 			Allowed:    false,
 			ReasonCode: "domain_not_allowed",
-			Reason:     "command path not in rule allow list",
+			Reason:     fmt.Sprintf("command path %q not in allow list %v", path, r.Allow),
 		}
 	}
 
@@ -151,7 +151,7 @@ func (e *Engine) EvaluateOne(cmd *cobra.Command) Decision {
 			return Decision{
 				Allowed:    false,
 				ReasonCode: reasonCodeForRisk(cmdRisk),
-				Reason:     "command risk exceeds rule max_risk",
+				Reason:     fmt.Sprintf("command risk %q exceeds rule max_risk %q", cmdRisk, r.MaxRisk),
 			}
 		}
 	}
@@ -163,7 +163,7 @@ func (e *Engine) EvaluateOne(cmd *cobra.Command) Decision {
 			return Decision{
 				Allowed:    false,
 				ReasonCode: "identity_mismatch",
-				Reason:     "command identities do not intersect rule identities",
+				Reason:     fmt.Sprintf("command supports identities %v; rule allows %v", cmdIdents, r.Identities),
 			}
 		}
 	}
@@ -348,12 +348,20 @@ func reasonCodeForRisk(risk platform.Risk) string {
 // Invalid globs are skipped here -- they're rejected upstream by
 // ValidateRule when the rule first enters the system.
 func matchesAny(globs []string, path string) bool {
+	_, ok := firstMatch(globs, path)
+	return ok
+}
+
+// firstMatch returns the first glob in globs that matches path. Used by
+// command_denylisted so the envelope can name the specific deny pattern
+// that fired.
+func firstMatch(globs []string, path string) (string, bool) {
 	for _, g := range globs {
 		if ok, err := doublestar.Match(g, path); err == nil && ok {
-			return true
+			return g, true
 		}
 	}
-	return false
+	return "", false
 }
 
 // hasIdentityIntersection reports whether the rule's typed identities
diff --git a/internal/cmdpolicy/engine_test.go b/internal/cmdpolicy/engine_test.go
index c102b58fd..3d35d3647 100644
--- a/internal/cmdpolicy/engine_test.go
+++ b/internal/cmdpolicy/engine_test.go
@@ -324,6 +324,64 @@ func TestEvaluate_identitiesIntersection(t *testing.T) {
 	}
 }
 
+// Reason strings must carry both the attempted value and the rule's
+// constraint so the envelope is self-contained for AI consumers.
+// Asserting on substrings (not exact match) leaves room for minor wording
+// tweaks while pinning the value-carrying behaviour.
+func TestEvaluate_reasonCarriesAttemptAndConstraint(t *testing.T) {
+	root := buildTree()
+
+	cases := []struct {
+		name        string
+		rule        *platform.Rule
+		path        string
+		wantInReason []string
+	}{
+		{
+			name:         "identity_mismatch surfaces both identity sets",
+			rule:         &platform.Rule{Identities: []platform.Identity{"bot"}},
+			path:         "docs/+update", // identities=[user]
+			wantInReason: []string{"[user]", "[bot]"},
+		},
+		{
+			name:         "domain_not_allowed surfaces path and allow list",
+			rule:         &platform.Rule{Allow: []string{"docs/**"}},
+			path:         "im/+send",
+			wantInReason: []string{`"im/+send"`, "docs/**"},
+		},
+		{
+			name:         "command_denylisted surfaces matched deny pattern",
+			rule:         &platform.Rule{Deny: []string{"docs/+delete-*"}},
+			path:         "docs/+delete-doc",
+			wantInReason: []string{`"docs/+delete-doc"`, `"docs/+delete-*"`},
+		},
+		{
+			name:         "risk_too_high surfaces cmd risk and max_risk",
+			rule:         &platform.Rule{MaxRisk: "write"},
+			path:         "docs/+delete-doc", // risk=high-risk-write
+			wantInReason: []string{`"high-risk-write"`, `"write"`},
+		},
+	}
+
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			got := cmdpolicy.New(tc.rule).EvaluateAll(root)
+			d, ok := got[tc.path]
+			if !ok {
+				t.Fatalf("no decision for %q", tc.path)
+			}
+			if d.Allowed {
+				t.Fatalf("%q should have been denied", tc.path)
+			}
+			for _, sub := range tc.wantInReason {
+				if !strings.Contains(d.Reason, sub) {
+					t.Errorf("reason %q missing %q", d.Reason, sub)
+				}
+			}
+		})
+	}
+}
+
 // Unknown identities defaults to ALLOW. A command with risk annotated
 // but without supportedIdentities passes any identity filter.
 func TestEvaluate_unknownIdentitiesIsAllow(t *testing.T) {