diff --git a/pdl-live-react/src-tauri/src/pdl/ast.rs b/pdl-live-react/src-tauri/src/pdl/ast.rs
index 599304208..32666ddee 100644
--- a/pdl-live-react/src-tauri/src/pdl/ast.rs
+++ b/pdl-live-react/src-tauri/src/pdl/ast.rs
@@ -519,6 +519,23 @@ pub enum StringOrBoolean {
     Boolean(bool),
 }
 
+#[derive(Serialize, Deserialize, Debug, Clone)]
+pub struct Expr<S, T> {
+    #[serde(rename = "pdl__expr")]
+    pub pdl_expr: S,
+
+    #[serde(rename = "pdl__result", skip_serializing_if = "Option::is_none")]
+    pub pdl_result: Option<T>,
+}
+
+#[derive(Serialize, Deserialize, Debug, Clone)]
+#[serde(untagged)]
+pub enum EvalsTo<S, T> {
+    Const(T),
+    Jinja(String),
+    Expr(Expr<S, T>),
+}
+
 /// Conditional control structure.
 ///
 /// Example:
@@ -535,7 +552,7 @@ pub enum StringOrBoolean {
 pub struct IfBlock {
     /// The condition to check
     #[serde(rename = "if")]
-    pub condition: StringOrBoolean,
+    pub condition: EvalsTo<StringOrBoolean, bool>,
 
     /// Branch to execute if the condition is true
     pub then: Box<PdlBlock>,
diff --git a/pdl-live-react/src-tauri/src/pdl/interpreter.rs b/pdl-live-react/src-tauri/src/pdl/interpreter.rs
index ba834127e..5d7a5120d 100644
--- a/pdl-live-react/src-tauri/src/pdl/interpreter.rs
+++ b/pdl-live-react/src-tauri/src/pdl/interpreter.rs
@@ -21,10 +21,10 @@ use serde_json::{from_str, json, to_string, Value};
 use serde_norway::{from_reader, from_str as from_yaml_str};
 
 use crate::pdl::ast::{
-    ArrayBlock, CallBlock, Closure, DataBlock, EmptyBlock, FunctionBlock, IfBlock, ImportBlock,
-    IncludeBlock, ListOrString, MessageBlock, ModelBlock, ObjectBlock, PdlBlock, PdlParser,
-    PdlResult, PdlUsage, PythonCodeBlock, ReadBlock, RepeatBlock, Role, Scope, SequencingBlock,
-    StringOrBoolean, StringOrNull,
+    ArrayBlock, CallBlock, Closure, DataBlock, EmptyBlock, EvalsTo, Expr, FunctionBlock, IfBlock,
+    ImportBlock, IncludeBlock, ListOrString, MessageBlock, ModelBlock, ObjectBlock, PdlBlock,
+    PdlParser, PdlResult, PdlUsage, PythonCodeBlock, ReadBlock, RepeatBlock, Role, Scope,
+    SequencingBlock, StringOrBoolean, StringOrNull,
 };
 
 type Messages = Vec<ChatMessage>;
@@ -207,6 +207,33 @@ impl<'a> Interpreter<'a> {
         }))
     }
 
+    /// Evaluate an Expr to a bool
+    fn eval_to_bool(
+        &self,
+        expr: &EvalsTo<StringOrBoolean, bool>,
+        state: &State,
+    ) -> Result<bool, PdlError> {
+        match expr {
+            EvalsTo::Const(b)
+            | EvalsTo::Expr(Expr {
+                pdl_expr: StringOrBoolean::Boolean(b),
+                ..
+            }) => Ok(b.clone()),
+
+            EvalsTo::Jinja(s)
+            | EvalsTo::Expr(Expr {
+                pdl_expr: StringOrBoolean::String(s),
+                ..
+            }) => match self.eval(s, state)? {
+                PdlResult::Bool(b) => Ok(b.clone()),
+                x => Err(Box::from(format!(
+                    "Expression {s} evaluated to non-boolean {:?}",
+                    x
+                ))),
+            },
+        }
+    }
+
     /// Evaluate String as a Jinja2 expression, expecting a string in response
     fn eval_to_string(&self, expr: &String, state: &State) -> Result<String, PdlError> {
         match self.eval(expr, state)? {
@@ -432,21 +459,13 @@ impl<'a> Interpreter<'a> {
             self.process_defs(&meta.defs, state).await?;
         }
 
-        let cond = match &block.condition {
-            StringOrBoolean::Boolean(b) => PdlResult::Bool(*b),
-            StringOrBoolean::String(s) => self.eval(s, state)?,
-        };
-
-        match cond {
-            PdlResult::Bool(true) => self.run_quiet(&block.then, state).await,
-            PdlResult::Bool(false) => match &block.else_ {
+        if self.eval_to_bool(&block.condition, state)? {
+            self.run_quiet(&block.then, state).await
+        } else {
+            match &block.else_ {
                 Some(else_block) => self.run_quiet(&else_block, state).await,
                 None => Ok(("".into(), vec![], PdlBlock::If(block.clone()))),
-            },
-            x => Err(Box::from(format!(
-                "if block condition evaluated to non-boolean value: {:?}",
-                x
-            ))),
+            }
         }
     }