diff --git a/crates/repl_eval/src/eval.rs b/crates/repl_eval/src/eval.rs
index 2af2a5fc7b..bb17149cf6 100644
--- a/crates/repl_eval/src/eval.rs
+++ b/crates/repl_eval/src/eval.rs
@@ -265,6 +265,8 @@ fn get_tags_vars_and_variant<'a>(
     (vars_of_tag, union_variant)
 }
 
+const FAKE_EXPR: &'static Loc<Expr> = &Loc::at_zero(Expr::Crash);
+
 fn expr_of_tag<'a, M: ReplAppMemory>(
     env: &mut Env<'a, '_>,
     mem: &'a M,
@@ -279,9 +281,35 @@ fn expr_of_tag<'a, M: ReplAppMemory>(
 
     debug_assert_eq!(arg_layouts.len(), arg_vars.len());
 
-    // NOTE assumes the data bytes are the first bytes
-    let it = arg_vars.iter().copied().zip(arg_layouts.iter());
-    let output = sequence_of_expr(env, mem, data_addr, it, when_recursive);
+    // The type checker stores payloads in definition order, but the memory representation sorts
+    // first by size (and tie-breaks by definition order).
+    let mut layouts: Vec<_> = arg_vars
+        .iter()
+        .enumerate()
+        .map(|(i, v)| {
+            let layout = env.layout_cache.from_var(env.arena, *v, env.subs).unwrap();
+            (i, *v, layout)
+        })
+        .collect_in(env.arena);
+
+    layouts.sort_by(|(i1, _, lay1), (i2, _, lay2)| {
+        cmp_fields(&env.layout_cache.interner, i1, *lay1, i2, *lay2)
+    });
+
+    let mut output: Vec<&Loc<Expr>> =
+        Vec::from_iter_in(std::iter::repeat(FAKE_EXPR).take(layouts.len()), env.arena);
+    let mut field_addr = data_addr;
+    for (i, var, lay) in layouts {
+        let repr = env.layout_cache.interner.get_repr(lay);
+        let expr = addr_to_ast(env, mem, field_addr, repr, when_recursive, var);
+        let loc_expr = Loc::at_zero(expr);
+
+        output[i] = &*env.arena.alloc(loc_expr);
+
+        // Advance the field pointer to the next field.
+        field_addr += env.layout_cache.interner.stack_size(lay) as usize;
+    }
+
     let output = output.into_bump_slice();
 
     Expr::Apply(loc_tag_expr, output, CalledVia::Space)
@@ -962,11 +990,14 @@ fn single_tag_union_to_ast<'a, M: ReplAppMemory>(
     let loc_tag_expr = &*arena.alloc(Loc::at_zero(tag_expr));
 
     let output = if field_layouts.len() == payload_vars.len() {
-        let it = payload_vars.iter().copied().zip(field_layouts);
+        let it = payload_vars
+            .iter()
+            .copied()
+            .zip(field_layouts.iter().copied());
         sequence_of_expr(env, mem, addr, it, WhenRecursive::Unreachable).into_bump_slice()
     } else if field_layouts.is_empty() && !payload_vars.is_empty() {
         // happens for e.g. `Foo Bar` where unit structures are nested and the inner one is dropped
-        let it = payload_vars.iter().copied().zip([&Layout::UNIT]);
+        let it = payload_vars.iter().copied().zip([Layout::UNIT]);
         sequence_of_expr(env, mem, addr, it, WhenRecursive::Unreachable).into_bump_slice()
     } else {
         unreachable!()
@@ -983,8 +1014,7 @@ fn sequence_of_expr<'a, 'env, I, M: ReplAppMemory>(
     when_recursive: WhenRecursive<'a>,
 ) -> Vec<'a, &'a Loc<Expr<'a>>>
 where
-    I: Iterator<Item = (Variable, &'a InLayout<'a>)>,
-    I: ExactSizeIterator<Item = (Variable, &'a InLayout<'a>)>,
+    I: ExactSizeIterator<Item = (Variable, InLayout<'a>)>,
 {
     let arena = env.arena;
     let mut output = Vec::with_capacity_in(sequence.len(), arena);
@@ -997,7 +1027,7 @@ where
             env,
             mem,
             field_addr,
-            env.layout_cache.get_repr(*layout),
+            env.layout_cache.get_repr(layout),
             when_recursive,
             var,
         );
@@ -1006,7 +1036,7 @@ where
         output.push(&*arena.alloc(loc_expr));
 
         // Advance the field pointer to the next field.
-        field_addr += env.layout_cache.interner.stack_size(*layout) as usize;
+        field_addr += env.layout_cache.interner.stack_size(layout) as usize;
     }
 
     output
diff --git a/crates/repl_test/src/tests.rs b/crates/repl_test/src/tests.rs
index 90b8d632b1..3769319140 100644
--- a/crates/repl_test/src/tests.rs
+++ b/crates/repl_test/src/tests.rs
@@ -1304,3 +1304,20 @@ fn nested_tuple() {
         r#"("a", (2, 3)) : ( Str, ( U32, U32 )a )a"#,
     );
 }
+
+#[test]
+fn ordered_tag_union_memory_layout() {
+    expect_success(
+        indoc!(
+            r#"
+            Loc : { line: U32, column: U32 }
+
+            Node : [ A Loc, Height U8 Loc ]
+
+            x : Node
+            x = Height 1 { line: 2, column: 3 }
+            "#
+        ),
+        r#""#,
+    );
+}