diff --git a/policy/compiler_test.go b/policy/compiler_test.go
index 7aa76bde..34c0b654 100644
--- a/policy/compiler_test.go
+++ b/policy/compiler_test.go
@@ -184,9 +184,10 @@ func compile(t testing.TB, name string, parseOpts []ParserOption, envOpts []cel.
 }
 
 func (r *runner) setup(t testing.TB) {
+	t.Helper()
 	env, ast, iss := compile(t, r.name, r.parseOpts, r.envOpts, r.compilerOpts)
 	if iss.Err() != nil {
-		t.Fatalf("Compile() failed: %v", iss.Err())
+		t.Fatalf("Compile(%s) failed: %v", r.name, iss.Err())
 	}
 	pExpr, err := cel.AstToString(ast)
 	if err != nil {
diff --git a/policy/composer.go b/policy/composer.go
index 8b134a36..be326ded 100644
--- a/policy/composer.go
+++ b/policy/composer.go
@@ -88,42 +88,34 @@ func (opt *ruleComposerImpl) Optimize(ctx *cel.OptimizerContext, a *ast.AST) *as
 }
 
 func (opt *ruleComposerImpl) optimizeRule(ctx *cel.OptimizerContext, r *CompiledRule) ast.Expr {
-	matchExpr := ctx.NewCall("optional.none")
-	matches := r.Matches()
-	matchCount := len(matches)
 	// Visitor to rewrite variables-prefixed identifiers with index names.
 	vars := r.Variables()
 	for _, v := range vars {
 		opt.registerVariable(ctx, v)
 	}
 
-	optionalResult := true
+	matches := r.Matches()
+	matchCount := len(matches)
+	var output compositionStep = nil
+	// If the rule has an optional output, the last result in the ternary should return
+	// `optional.none`. This output is implicit and created here to reflect the desired
+	// last possible output of this type of rule.
+	if r.HasOptionalOutput() {
+		output = newOptionalCompositionStep(ctx, ctx.NewLiteral(types.True), ctx.NewCall("optional.none"))
+	}
 	// Build the rule subgraph.
 	for i := matchCount - 1; i >= 0; i-- {
 		m := matches[i]
 		cond := ctx.CopyASTAndMetadata(m.Condition().NativeRep())
-		// If the condition is trivially true, not of the matches in the rule causes the result
-		// to become optional, and the rule is not the last match, then this will introduce
-		// unreachable outputs or rules.
-		triviallyTrue := m.ConditionIsLiteral(types.True)
 
-		// If the output is non-nil, then determine whether the output should be wrapped
-		// into an optional value, a conditional, or both.
+		// If the output is non-nil, then it is considered a non-optional output since
+		// it is explictly stated. If the rule itself is optional, then the base case value
+		// of output being optional.none() will convert the non-optional value to an optional
+		// one.
 		if m.Output() != nil {
 			out := ctx.CopyASTAndMetadata(m.Output().Expr().NativeRep())
-			if triviallyTrue {
-				matchExpr = out
-				optionalResult = false
-				continue
-			}
-			if optionalResult {
-				out = ctx.NewCall("optional.of", out)
-			}
-			matchExpr = ctx.NewCall(
-				operators.Conditional,
-				cond,
-				out,
-				matchExpr)
+			step := newNonOptionalCompositionStep(ctx, cond, out)
+			output = step.combine(output)
 			continue
 		}
 
@@ -132,29 +124,16 @@ func (opt *ruleComposerImpl) optimizeRule(ctx *cel.OptimizerContext, r *Compiled
 		child := m.NestedRule()
 		nestedRule := opt.optimizeRule(ctx, child)
 		nestedHasOptional := child.HasOptionalOutput()
-		if optionalResult && !nestedHasOptional {
-			nestedRule = ctx.NewCall("optional.of", nestedRule)
-		}
-		if !optionalResult && nestedHasOptional {
-			matchExpr = ctx.NewCall("optional.of", matchExpr)
-			optionalResult = true
-		}
-		// If either the nested rule or current condition output are optional then
-		// use optional.or() to specify the combination of the first and second results
-		// Note, the argument order is reversed due to the traversal of matches in
-		// reverse order.
-		if optionalResult && triviallyTrue {
-			matchExpr = ctx.NewMemberCall("or", nestedRule, matchExpr)
+		if nestedHasOptional {
+			step := newOptionalCompositionStep(ctx, cond, nestedRule)
+			output = step.combine(output)
 			continue
 		}
-		matchExpr = ctx.NewCall(
-			operators.Conditional,
-			cond,
-			nestedRule,
-			matchExpr,
-		)
+		step := newNonOptionalCompositionStep(ctx, cond, nestedRule)
+		output = step.combine(output)
 	}
 
+	matchExpr := output.expr()
 	identVisitor := opt.rewriteVariableName(ctx)
 	ast.PostOrderVisit(matchExpr, identVisitor)
 
@@ -177,6 +156,8 @@ func (opt *ruleComposerImpl) rewriteVariableName(ctx *cel.OptimizerContext) ast.
 	})
 }
 
+// registerVariable creates an entry for a variable name within the cel.@block used to enumerate
+// variables within composed policy expression.
 func (opt *ruleComposerImpl) registerVariable(ctx *cel.OptimizerContext, v *CompiledVariable) {
 	varName := fmt.Sprintf("variables.%s", v.Name())
 	indexVar := fmt.Sprintf("@index%d", opt.nextVarIndex)
@@ -192,6 +173,192 @@ func (opt *ruleComposerImpl) registerVariable(ctx *cel.OptimizerContext, v *Comp
 	opt.nextVarIndex++
 }
 
+// sortedVariables returns the variables ordered by their declaration index.
 func (opt *ruleComposerImpl) sortedVariables() []varIndex {
 	return opt.varIndices
 }
+
+// compositionStep interface represents an intermediate stage of rule and match expression composition
+//
+// The CompiledRule and CompiledMatch types are meant to represent standalone tuples of condition
+// and output expressions, and have no notion of how the order of combination would impact composition
+// since composition rules may vary based on the policy execution semantic, e.g. first-match versus
+// logical-or, logical-and, or accumulation.
+type compositionStep interface {
+	// isOptional indicates whether the output step has an optional result.
+	//
+	// Individual conditional attributes are not optional; however, rules and subrules can have optional output.
+	isOptional() bool
+
+	// condition returns the condition associated with the output.
+	condition() ast.Expr
+
+	// isConditional returns true if the condition expression is not trivially true.
+	isConditional() bool
+
+	// expr returns the output expression for the step.
+	expr() ast.Expr
+
+	// combine assembles two output expressions into a single output step.
+	combine(other compositionStep) compositionStep
+}
+
+// baseCompositionStep encapsulates the common features of an compositionStep implementation.
+type baseCompositionStep struct {
+	ctx  *cel.OptimizerContext
+	cond ast.Expr
+	out  ast.Expr
+}
+
+func (b baseCompositionStep) condition() ast.Expr {
+	return b.cond
+}
+
+func (b baseCompositionStep) isConditional() bool {
+	c := b.cond
+	return c.Kind() != ast.LiteralKind || c.AsLiteral() != types.True
+}
+
+func (b baseCompositionStep) expr() ast.Expr {
+	return b.out
+}
+
+// newNonOptionalCompositionStep returns an output step whose output is not optional.
+func newNonOptionalCompositionStep(ctx *cel.OptimizerContext, cond, out ast.Expr) nonOptionalCompositionStep {
+	return nonOptionalCompositionStep{
+		baseCompositionStep: &baseCompositionStep{
+			ctx:  ctx,
+			cond: cond,
+			out:  out,
+		},
+	}
+}
+
+type nonOptionalCompositionStep struct {
+	*baseCompositionStep
+}
+
+// isOptional returns false
+func (nonOptionalCompositionStep) isOptional() bool {
+	return false
+}
+
+// combine assembles a new compositionStep from the target output step an an input output step.
+//
+// non-optional.combine(non-optional) // non-optional
+// (non-optional && conditional).combine(optional) // optional
+// (non-optional && unconditional).combine(optional) // non-optional
+//
+// The last combination case is unusual, but effectively it means that the non-optional value prunes away
+// the potential optional output.
+func (s nonOptionalCompositionStep) combine(step compositionStep) compositionStep {
+	if step == nil {
+		// The input `step` may be nil if this is the first compositionStep
+		return s
+	}
+	ctx := s.ctx
+	trueCondition := ctx.NewLiteral(types.True)
+	if step.isOptional() {
+		// If the step is optional, convert the non-optional value to an optional one and return a ternary
+		if s.isConditional() {
+			return newOptionalCompositionStep(ctx,
+				trueCondition,
+				ctx.NewCall(operators.Conditional,
+					s.condition(),
+					ctx.NewCall("optional.of", s.expr()),
+					step.expr()),
+			)
+		}
+		// The `step` is pruned away by a unconditional non-optional step `s`.
+		return s
+	}
+	return newNonOptionalCompositionStep(ctx,
+		trueCondition,
+		ctx.NewCall(operators.Conditional,
+			s.condition(),
+			s.expr(),
+			step.expr()))
+}
+
+// newOptionalCompositionStep returns an output step with an optional policy output.
+func newOptionalCompositionStep(ctx *cel.OptimizerContext, cond, out ast.Expr) optionalCompositionStep {
+	return optionalCompositionStep{
+		baseCompositionStep: &baseCompositionStep{
+			ctx:  ctx,
+			cond: cond,
+			out:  out,
+		},
+	}
+}
+
+type optionalCompositionStep struct {
+	*baseCompositionStep
+}
+
+// isOptional returns true.
+func (optionalCompositionStep) isOptional() bool {
+	return true
+}
+
+// combine assembles a new compositionStep from the target output step an an input output step.
+//
+// optional.combine(optional) // optional
+// (optional && conditional).combine(non-optional) // optional
+// (optional && unconditional).combine(non-optional) // non-optional
+//
+// The last combination case indicates that an optional value in one case should be resolved
+// to a non-optional value as
+func (s optionalCompositionStep) combine(step compositionStep) compositionStep {
+	if step == nil {
+		// This is likely unreachable for an optional step, but worth adding as a safeguard
+		return s
+	}
+	ctx := s.ctx
+	trueCondition := ctx.NewLiteral(types.True)
+	if step.isOptional() {
+		// Introduce a ternary to capture the conditional return when combining a
+		// conditional optional with another optional.
+		if s.isConditional() {
+			return newOptionalCompositionStep(ctx,
+				trueCondition,
+				ctx.NewCall(operators.Conditional,
+					s.condition(),
+					s.expr(),
+					step.expr()),
+			)
+		}
+		// When an optional is unconditionally combined with another optional, rely
+		// on the optional 'or' to fall-through from one optional to another.
+		if !isOptionalNone(step.expr()) {
+			return newOptionalCompositionStep(ctx,
+				trueCondition,
+				ctx.NewMemberCall("or", s.expr(), step.expr()))
+		}
+		// Otherwise, the current step 's' is unconditional and effectively prunes away
+		// the other input 'step'.
+		return s
+	}
+	if s.isConditional() {
+		// Introduce a ternary to capture the conditional return while wrapping the
+		// non-optional result from a lower step into an optional value.
+		return newOptionalCompositionStep(ctx,
+			trueCondition,
+			ctx.NewCall(operators.Conditional,
+				s.condition(),
+				s.expr(),
+				ctx.NewCall("optional.of", step.expr())))
+	}
+	// If the current step is unconditional and the step is non-optional, attempt
+	// to convert to the optional step 's' to a non-optional value using `orValue`
+	// with the 'step' expression value.
+	return newNonOptionalCompositionStep(ctx,
+		trueCondition,
+		ctx.NewMemberCall("orValue", s.expr(), step.expr()),
+	)
+}
+
+func isOptionalNone(e ast.Expr) bool {
+	return e.Kind() == ast.CallKind &&
+		e.AsCall().FunctionName() == "optional.none" &&
+		len(e.AsCall().Args()) == 0
+}
diff --git a/policy/helper_test.go b/policy/helper_test.go
index 0729dc9a..396d919c 100644
--- a/policy/helper_test.go
+++ b/policy/helper_test.go
@@ -57,9 +57,8 @@ var (
 	  ["us", "uk", "es"],
 	  {"us": false, "ru": false, "ir": false}],
 	  ((resource.origin in @index1 && !(resource.origin in @index0))
-	    ? optional.of({"banned": true}) : optional.none()).or(
-	      optional.of((resource.origin in @index0)
-	      ? {"banned": false} : {"banned": true})))`,
+	    ? optional.of({"banned": true}) : optional.none()).orValue(
+	     (resource.origin in @index0) ? {"banned": false} : {"banned": true}))`,
 		},
 		{
 			name: "nested_rule2",
@@ -86,6 +85,33 @@ var (
 		: (!(resource.origin in @index0)
 		  ? optional.of({"banned": "unconfigured_region"}) : optional.none()))`,
 		},
+		{
+			name: "nested_rule4",
+			expr: `(x > 0) ? true : false`,
+		},
+		{
+			name: "nested_rule5",
+			expr: `
+	(x > 0)
+	  ? ((x > 2) ? optional.of(true) : optional.none())
+	  : ((x > 1)
+	    ? ((x >= 2) ? optional.of(true) : optional.none())
+		: optional.of(false))`,
+		},
+		{
+			name: "nested_rule6",
+			expr: `
+	((x > 2) ? optional.of(true) : optional.none())
+	  .orValue(((x > 3) ? optional.of(true) : optional.none())
+	  .orValue(false))`,
+		},
+		{
+			name: "nested_rule7",
+			expr: `
+	((x > 2) ? optional.of(true) : optional.none())
+	.or(((x > 3) ? optional.of(true) : optional.none())
+	.or((x > 1) ? optional.of(false) : optional.none()))`,
+		},
 		{
 			name: "context_pb",
 			expr: `
diff --git a/policy/testdata/nested_rule4/config.yaml b/policy/testdata/nested_rule4/config.yaml
new file mode 100644
index 00000000..5afb8c58
--- /dev/null
+++ b/policy/testdata/nested_rule4/config.yaml
@@ -0,0 +1,19 @@
+# Copyright 2024 Google LLC
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#    https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+name: "nested_rule4"
+variables:
+  - name: x
+    type:
+      type_name: int
diff --git a/policy/testdata/nested_rule4/policy.yaml b/policy/testdata/nested_rule4/policy.yaml
new file mode 100644
index 00000000..ea53bfb2
--- /dev/null
+++ b/policy/testdata/nested_rule4/policy.yaml
@@ -0,0 +1,24 @@
+# Copyright 2024 Google LLC
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#    https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+name: nested_rule4
+rule:
+  match:
+    - condition: x > 0
+      rule:
+        match:
+          - rule:
+              match:
+                - output: "true"
+    - output: "false"
diff --git a/policy/testdata/nested_rule4/tests.yaml b/policy/testdata/nested_rule4/tests.yaml
new file mode 100644
index 00000000..a5af137f
--- /dev/null
+++ b/policy/testdata/nested_rule4/tests.yaml
@@ -0,0 +1,28 @@
+# Copyright 2024 Google LLC
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#    https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+description: "Nested rule tests which explore optional vs non-optional returns"
+section:
+  - name: "valid"
+    tests:
+      - name: "x=0"
+        input:
+          x:
+            value: 0
+        output: "false"
+      - name: "x=2"
+        input:
+          x:
+            value: 2
+        output: "true"
diff --git a/policy/testdata/nested_rule5/config.yaml b/policy/testdata/nested_rule5/config.yaml
new file mode 100644
index 00000000..49945009
--- /dev/null
+++ b/policy/testdata/nested_rule5/config.yaml
@@ -0,0 +1,19 @@
+# Copyright 2024 Google LLC
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#    https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+name: "nested_rule5"
+variables:
+  - name: x
+    type:
+      type_name: int
diff --git a/policy/testdata/nested_rule5/policy.yaml b/policy/testdata/nested_rule5/policy.yaml
new file mode 100644
index 00000000..e43dce18
--- /dev/null
+++ b/policy/testdata/nested_rule5/policy.yaml
@@ -0,0 +1,30 @@
+# Copyright 2024 Google LLC
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#    https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+name: nested_rule5
+rule:
+  match:
+    - condition: x > 0
+      rule:
+        match:
+          - rule:
+              match:
+                - condition: "x > 2"
+                  output: "true"
+    - condition: x > 1
+      rule:
+        match:
+          - condition: "x >= 2"
+            output: "true"
+    - output: "false"
diff --git a/policy/testdata/nested_rule5/tests.yaml b/policy/testdata/nested_rule5/tests.yaml
new file mode 100644
index 00000000..66cc4450
--- /dev/null
+++ b/policy/testdata/nested_rule5/tests.yaml
@@ -0,0 +1,38 @@
+# Copyright 2024 Google LLC
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#    https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+description: "Nested rule tests which explore optional vs non-optional returns"
+section:
+  - name: "valid"
+    tests:
+      - name: "x=0"
+        input:
+          x:
+            value: 0
+        output: "false"
+      - name: "x=1"
+        input:
+          x:
+            value: 1
+        output: "optional.none()"
+      - name: "x=2"
+        input:
+          x:
+            value: 2
+        output: "optional.none()"
+      - name: "x=3"
+        input:
+          x:
+            value: 3
+        output: "true"
diff --git a/policy/testdata/nested_rule6/config.yaml b/policy/testdata/nested_rule6/config.yaml
new file mode 100644
index 00000000..a5b1ee16
--- /dev/null
+++ b/policy/testdata/nested_rule6/config.yaml
@@ -0,0 +1,19 @@
+# Copyright 2024 Google LLC
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#    https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+name: "nested_rule6"
+variables:
+  - name: x
+    type:
+      type_name: int
diff --git a/policy/testdata/nested_rule6/policy.yaml b/policy/testdata/nested_rule6/policy.yaml
new file mode 100644
index 00000000..a3360e7c
--- /dev/null
+++ b/policy/testdata/nested_rule6/policy.yaml
@@ -0,0 +1,28 @@
+# Copyright 2024 Google LLC
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#    https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+name: nested_rule6
+rule:
+  match:
+    - rule:
+        match:
+          - rule:
+              match:
+                - condition: "x > 2"
+                  output: "true"
+    - rule:
+        match:
+          - condition: "x > 3"
+            output: "true"
+    - output: "false"
diff --git a/policy/testdata/nested_rule6/tests.yaml b/policy/testdata/nested_rule6/tests.yaml
new file mode 100644
index 00000000..dabce623
--- /dev/null
+++ b/policy/testdata/nested_rule6/tests.yaml
@@ -0,0 +1,23 @@
+# Copyright 2024 Google LLC
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#    https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+description: "Nested rule tests which explore optional vs non-optional returns"
+section:
+  - name: "valid"
+    tests:
+      - name: "x=0"
+        input:
+          x:
+            value: 0
+        output: "false"
diff --git a/policy/testdata/nested_rule7/config.yaml b/policy/testdata/nested_rule7/config.yaml
new file mode 100644
index 00000000..74d4d8c2
--- /dev/null
+++ b/policy/testdata/nested_rule7/config.yaml
@@ -0,0 +1,19 @@
+# Copyright 2024 Google LLC
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#    https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+name: "nested_rule7"
+variables:
+  - name: x
+    type:
+      type_name: int
diff --git a/policy/testdata/nested_rule7/policy.yaml b/policy/testdata/nested_rule7/policy.yaml
new file mode 100644
index 00000000..fcacd017
--- /dev/null
+++ b/policy/testdata/nested_rule7/policy.yaml
@@ -0,0 +1,29 @@
+# Copyright 2024 Google LLC
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#    https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+name: nested_rule7
+rule:
+  match:
+    - rule:
+        match:
+          - rule:
+              match:
+                - condition: "x > 2"
+                  output: "true"
+    - rule:
+        match:
+          - condition: "x > 3"
+            output: "true"
+    - condition: "x > 1"
+      output: "false"
diff --git a/policy/testdata/nested_rule7/tests.yaml b/policy/testdata/nested_rule7/tests.yaml
new file mode 100644
index 00000000..7844e18f
--- /dev/null
+++ b/policy/testdata/nested_rule7/tests.yaml
@@ -0,0 +1,38 @@
+# Copyright 2024 Google LLC
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#    https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+description: "Nested rule tests which explore optional vs non-optional returns"
+section:
+  - name: "valid"
+    tests:
+     - name: "x=1"
+       input:
+          x:
+            value: 1
+       output: "optional.none()"
+     - name: "x=2"
+       input:
+          x:
+            value: 2
+       output: "false"
+     - name: "x=3"
+       input:
+          x:
+            value: 3
+       output: "true"
+     - name: "x=4"
+       input:
+          x:
+            value: 4
+       output: "true"