diff --git a/R/relational-duckdb.R b/R/relational-duckdb.R
index b3139c9b..5af09280 100644
--- a/R/relational-duckdb.R
+++ b/R/relational-duckdb.R
@@ -15,6 +15,9 @@ get_default_duckdb_connection <- function() {
 }
 
 duckplyr_macros <- c(
+  # https://github.com/duckdb/duckdb-r/pull/156
+  "___null" = "() AS CAST(NULL AS BOOLEAN)",
+
   "<" = '(x, y) AS "r_base::<"(x, y)',
   "<=" = '(x, y) AS "r_base::<="(x, y)',
   ">" = '(x, y) AS "r_base::>"(x, y)',
diff --git a/R/relational.R b/R/relational.R
index 7d32bca1..cfd4ecf7 100644
--- a/R/relational.R
+++ b/R/relational.R
@@ -118,9 +118,10 @@ rel_translate <- function(
 
     switch(typeof(expr),
       character = ,
-      logical = ,
       integer = ,
       double = relexpr_constant(expr),
+      # https://github.com/duckdb/duckdb-r/pull/156
+      logical = if (is.na(expr)) relexpr_function("___null", list()) else relexpr_constant(expr),
       #
       symbol = {
         if (as.character(expr) %in% names_forbidden) {