diff --git a/hipcheck/src/analysis/score.rs b/hipcheck/src/analysis/score.rs
index 4817af08..ed6b073f 100644
--- a/hipcheck/src/analysis/score.rs
+++ b/hipcheck/src/analysis/score.rs
@@ -279,8 +279,8 @@ pub fn score_results(_phase: &SpinnerPhase, db: &dyn ScoringProvider) -> Result<
 			// Determine if analysis passed by evaluating policy expr
 			let passed = {
 				if let Ok(output) = &response {
-					Executor::std()
-						.run(analysis.1.as_str(), &output.value)
+					Executor::std(output.value.clone())
+						.run(analysis.1.as_str())
 						.map_err(|e| hc_error!("{}", e))?
 				} else {
 					false
diff --git a/hipcheck/src/policy_exprs/env.rs b/hipcheck/src/policy_exprs/env.rs
index 98605cd9..2ae25919 100644
--- a/hipcheck/src/policy_exprs/env.rs
+++ b/hipcheck/src/policy_exprs/env.rs
@@ -2,6 +2,7 @@
 
 use crate::policy_exprs::{eval, Error, Expr, Ident, Primitive, Result, F64};
 use itertools::Itertools as _;
+use serde_json::Value;
 use std::{cmp::Ordering, collections::HashMap, ops::Not as _};
 use Expr::*;
 use Primitive::*;
@@ -13,6 +14,8 @@ pub struct Env<'parent> {
 
 	/// Possible pointer to parent, for lexical scope.
 	parent: Option<&'parent Env<'parent>>,
+
+	pub context: Value,
 }
 
 /// A binding in the environment.
@@ -30,16 +33,17 @@ type Op = fn(&Env, &[Expr]) -> Result<Expr>;
 
 impl<'parent> Env<'parent> {
 	/// Create an empty environment.
-	fn empty() -> Self {
+	fn empty(context: Value) -> Self {
 		Env {
 			bindings: HashMap::new(),
 			parent: None,
+			context,
 		}
 	}
 
 	/// Create the standard environment.
-	pub fn std() -> Self {
-		let mut env = Env::empty();
+	pub fn std(context: Value) -> Self {
+		let mut env = Env::empty(context);
 
 		// Comparison functions.
 		env.add_fn("gt", gt);
@@ -87,6 +91,7 @@ impl<'parent> Env<'parent> {
 		Env {
 			bindings: HashMap::new(),
 			parent: Some(self),
+			context: self.context.clone(),
 		}
 	}
 
diff --git a/hipcheck/src/policy_exprs/expr.rs b/hipcheck/src/policy_exprs/expr.rs
index b1e00740..38c6a8c5 100644
--- a/hipcheck/src/policy_exprs/expr.rs
+++ b/hipcheck/src/policy_exprs/expr.rs
@@ -58,8 +58,8 @@ pub struct Ident(pub String);
 /// A late-binding for a JSON pointer
 #[derive(Debug, Clone, PartialEq, Eq)]
 pub struct JsonPointer {
-	pointer: String,
-	value: Option<serde_json::Value>,
+	pub pointer: String,
+	pub value: Option<serde_json::Value>,
 }
 
 /// A non-NaN 64-bit floating point number.
diff --git a/hipcheck/src/policy_exprs/json_pointer.rs b/hipcheck/src/policy_exprs/json_pointer.rs
index b655799f..ddd21b21 100644
--- a/hipcheck/src/policy_exprs/json_pointer.rs
+++ b/hipcheck/src/policy_exprs/json_pointer.rs
@@ -77,7 +77,7 @@ fn process_pointer(pointer: &str, context: &Value) -> Result<String> {
 }
 
 /// Wrap serde_json's `Value::pointer` method to provide better error handling.
-fn lookup_json_pointer<'val>(pointer: &str, context: &'val Value) -> Result<&'val Value> {
+pub fn lookup_json_pointer<'val>(pointer: &str, context: &'val Value) -> Result<&'val Value> {
 	// serde_json's JSON Pointer implementation does not distinguish between
 	// syntax errors and lookup errors, so we check the syntax ourselves.
 	// The only syntax error that serde_json currently recognizes is that a
@@ -101,11 +101,15 @@ fn lookup_json_pointer<'val>(pointer: &str, context: &'val Value) -> Result<&'va
 /// Attempt to interpret a JSON Value as a Policy Expression.
 /// `pointer` and `context` are only passed in to provide more context in the
 /// case of errors.
-fn json_to_policy_expr(val: &Value, pointer: &str, context: &Value) -> Result<Expr> {
+pub fn json_to_policy_expr(val: &Value, pointer: &str, context: &Value) -> Result<Expr> {
 	match val {
 		Value::Number(n) => {
-			let not_nan = NotNan::new(n.as_f64().unwrap()).unwrap();
-			Ok(Expr::Primitive(Primitive::Float(not_nan)))
+			if n.is_i64() {
+				Ok(Expr::Primitive(Primitive::Int(n.as_i64().unwrap())))
+			} else {
+				let not_nan = NotNan::new(n.as_f64().unwrap()).unwrap();
+				Ok(Expr::Primitive(Primitive::Float(not_nan)))
+			}
 		}
 		Value::Bool(b) => Ok(Expr::Primitive(Primitive::Bool(*b))),
 		Value::Array(a) => {
diff --git a/hipcheck/src/policy_exprs/mod.rs b/hipcheck/src/policy_exprs/mod.rs
index c030275e..5b44a2c3 100644
--- a/hipcheck/src/policy_exprs/mod.rs
+++ b/hipcheck/src/policy_exprs/mod.rs
@@ -17,6 +17,7 @@ pub use crate::policy_exprs::{
 	token::LexingError,
 };
 use env::Binding;
+use expr::JsonPointer;
 pub use expr::{parse, Primitive};
 use json_pointer::process_json_pointers;
 use serde_json::Value;
@@ -29,22 +30,23 @@ pub struct Executor {
 
 impl Executor {
 	/// Create an `Executor` with the standard set of functions defined.
-	pub fn std() -> Self {
-		Executor { env: Env::std() }
+	pub fn std(context: Value) -> Self {
+		Executor {
+			env: Env::std(context),
+		}
 	}
 
 	/// Run a `deke` program.
-	pub fn run(&self, raw_program: &str, context: &Value) -> Result<bool> {
-		match self.parse_and_eval(raw_program, context)? {
+	pub fn run(&self, raw_program: &str) -> Result<bool> {
+		match self.parse_and_eval(raw_program)? {
 			Expr::Primitive(Primitive::Bool(b)) => Ok(b),
 			result => Err(Error::DidNotReturnBool(result)),
 		}
 	}
 
 	/// Run a `deke` program, but don't try to convert the result to a `bool`.
-	pub fn parse_and_eval(&self, raw_program: &str, context: &Value) -> Result<Expr> {
-		let processed_program = process_json_pointers(raw_program, context)?;
-		let program = parse(&processed_program)?;
+	pub fn parse_and_eval(&self, raw_program: &str) -> Result<Expr> {
+		let program = parse(raw_program)?;
 		let expr = eval(&self.env, &program)?;
 		Ok(expr)
 	}
@@ -67,7 +69,11 @@ pub(crate) fn eval(env: &Env, program: &Expr) -> Result<Expr> {
 			}
 		}
 		Expr::Lambda(_, body) => Ok((**body).clone()),
-		Expr::JsonPointer(_) => unreachable!(),
+		Expr::JsonPointer(JsonPointer { pointer, .. }) => {
+			let val = json_pointer::lookup_json_pointer(pointer, &env.context)?;
+			let expr = json_pointer::json_to_policy_expr(val, pointer, &env.context)?;
+			Ok(expr)
+		}
 	};
 
 	log::debug!("input: {program:?}, output: {output:?}");
@@ -78,13 +84,14 @@ pub(crate) fn eval(env: &Env, program: &Expr) -> Result<Expr> {
 #[cfg(test)]
 mod tests {
 	use super::*;
+	use serde_json::json;
 	use test_log::test;
 
 	#[test]
 	fn run_bool() {
 		let program = "#t";
 		let context = Value::Null;
-		let is_true = Executor::std().run(program, &context).unwrap();
+		let is_true = Executor::std(context).run(program).unwrap();
 		assert!(is_true);
 	}
 
@@ -92,7 +99,7 @@ mod tests {
 	fn run_basic() {
 		let program = "(eq (add 1 2) 3)";
 		let context = Value::Null;
-		let is_true = Executor::std().run(program, &context).unwrap();
+		let is_true = Executor::std(context).run(program).unwrap();
 		assert!(is_true);
 	}
 
@@ -100,7 +107,7 @@ mod tests {
 	fn eval_basic() {
 		let program = "(add 1 2)";
 		let context = Value::Null;
-		let result = Executor::std().parse_and_eval(program, &context).unwrap();
+		let result = Executor::std(context).parse_and_eval(program).unwrap();
 		assert_eq!(result, Expr::Primitive(Primitive::Int(3)));
 	}
 
@@ -108,7 +115,7 @@ mod tests {
 	fn eval_divz_int_zero() {
 		let program = "(divz 1 0)";
 		let context = Value::Null;
-		let result = Executor::std().parse_and_eval(program, &context).unwrap();
+		let result = Executor::std(context).parse_and_eval(program).unwrap();
 		assert_eq!(
 			result,
 			Expr::Primitive(Primitive::Float(F64::new(0.0).unwrap()))
@@ -119,7 +126,7 @@ mod tests {
 	fn eval_divz_int() {
 		let program = "(divz 1 2)";
 		let context = Value::Null;
-		let result = Executor::std().parse_and_eval(program, &context).unwrap();
+		let result = Executor::std(context).parse_and_eval(program).unwrap();
 		assert_eq!(
 			result,
 			Expr::Primitive(Primitive::Float(F64::new(0.5).unwrap()))
@@ -130,7 +137,7 @@ mod tests {
 	fn eval_divz_float() {
 		let program = "(divz 1.0 2.0)";
 		let context = Value::Null;
-		let result = Executor::std().parse_and_eval(program, &context).unwrap();
+		let result = Executor::std(context).parse_and_eval(program).unwrap();
 		assert_eq!(
 			result,
 			Expr::Primitive(Primitive::Float(F64::new(0.5).unwrap()))
@@ -141,7 +148,7 @@ mod tests {
 	fn eval_divz_float_zero() {
 		let program = "(divz 1.0 0.0)";
 		let context = Value::Null;
-		let result = Executor::std().parse_and_eval(program, &context).unwrap();
+		let result = Executor::std(context).parse_and_eval(program).unwrap();
 		assert_eq!(
 			result,
 			Expr::Primitive(Primitive::Float(F64::new(0.0).unwrap()))
@@ -152,7 +159,7 @@ mod tests {
 	fn eval_bools() {
 		let program = "(neq 1 2)";
 		let context = Value::Null;
-		let result = Executor::std().parse_and_eval(program, &context).unwrap();
+		let result = Executor::std(context).parse_and_eval(program).unwrap();
 		assert_eq!(result, Expr::Primitive(Primitive::Bool(true)));
 	}
 
@@ -160,7 +167,7 @@ mod tests {
 	fn eval_array() {
 		let program = "(max [1 4 6 10 2 3 0])";
 		let context = Value::Null;
-		let result = Executor::std().parse_and_eval(program, &context).unwrap();
+		let result = Executor::std(context).parse_and_eval(program).unwrap();
 		assert_eq!(result, Expr::Primitive(Primitive::Int(10)));
 	}
 
@@ -168,7 +175,7 @@ mod tests {
 	fn run_array() {
 		let program = "(eq 7 (count [1 4 6 10 2 3 0]))";
 		let context = Value::Null;
-		let is_true = Executor::std().run(program, &context).unwrap();
+		let is_true = Executor::std(context).run(program).unwrap();
 		assert!(is_true);
 	}
 
@@ -176,7 +183,7 @@ mod tests {
 	fn eval_higher_order_func() {
 		let program = "(eq 3 (count (filter (gt 8.0) [1.0 2.0 10.0 20.0 30.0])))";
 		let context = Value::Null;
-		let result = Executor::std().parse_and_eval(program, &context).unwrap();
+		let result = Executor::std(context).parse_and_eval(program).unwrap();
 		assert_eq!(result, Expr::Primitive(Primitive::Bool(true)));
 	}
 
@@ -185,7 +192,7 @@ mod tests {
 		let program =
 			"(eq 3 (count (filter (gt 8.0) (foreach (sub 1.0) [1.0 2.0 10.0 20.0 30.0]))))";
 		let context = Value::Null;
-		let result = Executor::std().parse_and_eval(program, &context).unwrap();
+		let result = Executor::std(context).parse_and_eval(program).unwrap();
 		assert_eq!(result, Expr::Primitive(Primitive::Bool(true)));
 	}
 
@@ -193,7 +200,7 @@ mod tests {
 	fn eval_basic_filter() {
 		let program = "(filter (eq 0) [1 0 1 0 0 1 2])";
 		let context = Value::Null;
-		let result = Executor::std().parse_and_eval(program, &context).unwrap();
+		let result = Executor::std(context).parse_and_eval(program).unwrap();
 		assert_eq!(
 			result,
 			Expr::Array(vec![
@@ -203,4 +210,35 @@ mod tests {
 			])
 		);
 	}
+
+	#[test]
+	fn eval_basic_json_pointer_root_bool() {
+		let program = "$";
+		let context = Value::Bool(true);
+		let result = Executor::std(context).parse_and_eval(program).unwrap();
+		assert_eq!(result, Expr::Primitive(Primitive::Bool(true)));
+	}
+
+	#[test]
+	fn eval_basic_json_pointer_i64() {
+		let program = "$/answer";
+		let context = json!({
+			"answer": 42,
+		});
+		let result = Executor::std(context).parse_and_eval(program).unwrap();
+		assert_eq!(result, Expr::Primitive(Primitive::Int(42)));
+	}
+
+	#[test]
+	fn eval_basic_json_pointer_f64() {
+		let program = "$/number";
+		let context = json!({
+			"number": 7.3,
+		});
+		let result = Executor::std(context).parse_and_eval(program).unwrap();
+		assert_eq!(
+			result,
+			Expr::Primitive(Primitive::Float(F64::new(7.3).unwrap()))
+		);
+	}
 }
diff --git a/hipcheck/src/report/mod.rs b/hipcheck/src/report/mod.rs
index 96c9a458..ad3a09d8 100644
--- a/hipcheck/src/report/mod.rs
+++ b/hipcheck/src/report/mod.rs
@@ -687,8 +687,8 @@ impl RecommendationKind {
 	fn is(risk_score: RiskScore, risk_policy: RiskPolicy) -> Result<RecommendationKind> {
 		let value = serde_json::to_value(risk_score.0).unwrap();
 		Ok(
-			if Executor::std()
-				.run(&risk_policy.0, &value)
+			if Executor::std(value)
+				.run(&risk_policy.0)
 				.context("investigate policy expression execution failed")?
 			{
 				RecommendationKind::Pass