diff --git a/lib/expr.ex b/lib/expr.ex
index a9a152d..f4fd42b 100644
--- a/lib/expr.ex
+++ b/lib/expr.ex
@@ -344,28 +344,37 @@ defmodule AshPostgres.Expr do
     when_true =
       do_dynamic_expr(query, when_true, bindings, pred_embedded? || embedded?, when_true_type)
 
-    when_false =
-      do_dynamic_expr(
-        query,
-        when_false,
-        bindings,
-        pred_embedded? || embedded?,
-        when_false_type
-      )
+    {additional_cases, when_false} =
+      extract_cases(query, when_false, bindings, pred_embedded? || embedded?, when_false_type)
+
+    additional_case_fragments =
+      additional_cases
+      |> Enum.flat_map(fn {condition, when_true} ->
+        [
+          raw: " WHEN ",
+          casted_expr: condition,
+          raw: " THEN ",
+          casted_expr: when_true
+        ]
+      end)
 
     do_dynamic_expr(
       query,
       %Fragment{
         embedded?: pred_embedded?,
-        arguments: [
-          raw: "(CASE WHEN ",
-          casted_expr: condition,
-          raw: " THEN ",
-          casted_expr: when_true,
-          raw: " ELSE ",
-          casted_expr: when_false,
-          raw: " END)"
-        ]
+        arguments:
+          [
+            raw: "(CASE WHEN ",
+            casted_expr: condition,
+            raw: " THEN ",
+            casted_expr: when_true
+          ] ++
+            additional_case_fragments ++
+            [
+              raw: " ELSE ",
+              casted_expr: when_false,
+              raw: " END)"
+            ]
       },
       bindings,
       embedded?,
@@ -1376,6 +1385,81 @@ defmodule AshPostgres.Expr do
     end
   end
 
+  defp extract_cases(
+         query,
+         expr,
+         bindings,
+         embedded?,
+         type,
+         acc \\ []
+       )
+
+  defp extract_cases(
+         query,
+         %If{arguments: [condition, when_true, when_false], embedded?: pred_embedded?},
+         bindings,
+         embedded?,
+         type,
+         acc
+       ) do
+    [condition_type, when_true_type, when_false_type] =
+      case AshPostgres.Types.determine_types(If, [condition, when_true, when_false]) do
+        [condition_type, when_true] ->
+          [condition_type, when_true, nil]
+
+        [condition_type, when_true, when_false] ->
+          [condition_type, when_true, when_false]
+      end
+      |> case do
+        [condition_type, nil, nil] ->
+          [condition_type, type, type]
+
+        [condition_type, when_true, nil] ->
+          [condition_type, when_true, type]
+
+        [condition_type, nil, when_false] ->
+          [condition_type, type, when_false]
+
+        [condition_type, when_true, when_false] ->
+          [condition_type, when_true, when_false]
+      end
+
+    condition =
+      do_dynamic_expr(query, condition, bindings, pred_embedded? || embedded?, condition_type)
+
+    when_true =
+      do_dynamic_expr(query, when_true, bindings, pred_embedded? || embedded?, when_true_type)
+
+    extract_cases(
+      query,
+      when_false,
+      bindings,
+      embedded?,
+      when_false_type,
+      [{condition, when_true} | acc]
+    )
+  end
+
+  defp extract_cases(
+         query,
+         other,
+         bindings,
+         embedded?,
+         type,
+         acc
+       ) do
+    expr =
+      do_dynamic_expr(
+        query,
+        other,
+        bindings,
+        embedded?,
+        type
+      )
+
+    {Enum.reverse(acc), expr}
+  end
+
   defp split_at_paths(type, constraints, next, acc \\ [{:bracket, [], nil, nil}])
 
   defp split_at_paths(_type, _constraints, [], acc) do
diff --git a/mix.lock b/mix.lock
index 451389b..9e72318 100644
--- a/mix.lock
+++ b/mix.lock
@@ -1,5 +1,5 @@
 %{
-  "ash": {:hex, :ash, "2.17.13", "a3bb846238d4eb029da00583554f074d73950cfa4bc2f5964283d2e4491a9543", [:mix], [{:comparable, "~> 1.0", [hex: :comparable, repo: "hexpm", optional: false]}, {:decimal, "~> 2.0", [hex: :decimal, repo: "hexpm", optional: false]}, {:earmark, "~> 1.4", [hex: :earmark, repo: "hexpm", optional: false]}, {:ecto, "~> 3.7", [hex: :ecto, repo: "hexpm", optional: false]}, {:ets, "~> 0.8", [hex: :ets, repo: "hexpm", optional: false]}, {:jason, ">= 1.0.0", [hex: :jason, repo: "hexpm", optional: false]}, {:picosat_elixir, "~> 0.2", [hex: :picosat_elixir, repo: "hexpm", optional: false]}, {:plug, ">= 0.0.0", [hex: :plug, repo: "hexpm", optional: true]}, {:spark, ">= 1.1.50 and < 2.0.0-0", [hex: :spark, repo: "hexpm", optional: false]}, {:stream_data, "~> 0.6", [hex: :stream_data, repo: "hexpm", optional: false]}, {:telemetry, "~> 1.1", [hex: :telemetry, repo: "hexpm", optional: false]}], "hexpm", "b41a3e029b1553e71a0cab7db66d98a1ea7a883d301b866630ef9d09e64d38ee"},
+  "ash": {:hex, :ash, "2.17.14", "ccb68a0eacd7d4f4652a01baa3ceda510d793ab769c82958d644638905f08f7d", [:mix], [{:comparable, "~> 1.0", [hex: :comparable, repo: "hexpm", optional: false]}, {:decimal, "~> 2.0", [hex: :decimal, repo: "hexpm", optional: false]}, {:earmark, "~> 1.4", [hex: :earmark, repo: "hexpm", optional: false]}, {:ecto, "~> 3.7", [hex: :ecto, repo: "hexpm", optional: false]}, {:ets, "~> 0.8", [hex: :ets, repo: "hexpm", optional: false]}, {:jason, ">= 1.0.0", [hex: :jason, repo: "hexpm", optional: false]}, {:picosat_elixir, "~> 0.2", [hex: :picosat_elixir, repo: "hexpm", optional: false]}, {:plug, ">= 0.0.0", [hex: :plug, repo: "hexpm", optional: true]}, {:spark, ">= 1.1.50 and < 2.0.0-0", [hex: :spark, repo: "hexpm", optional: false]}, {:stream_data, "~> 0.6", [hex: :stream_data, repo: "hexpm", optional: false]}, {:telemetry, "~> 1.1", [hex: :telemetry, repo: "hexpm", optional: false]}], "hexpm", "b09a585924f222a1d353ebd13ec8691c4b9c5e37a8be271ee8960c34feb3fad0"},
   "benchee": {:hex, :benchee, "1.1.0", "f3a43817209a92a1fade36ef36b86e1052627fd8934a8b937ac9ab3a76c43062", [:mix], [{:deep_merge, "~> 1.0", [hex: :deep_merge, repo: "hexpm", optional: false]}, {:statistex, "~> 1.0", [hex: :statistex, repo: "hexpm", optional: false]}], "hexpm", "7da57d545003165a012b587077f6ba90b89210fd88074ce3c60ce239eb5e6d93"},
   "bunt": {:hex, :bunt, "0.2.0", "951c6e801e8b1d2cbe58ebbd3e616a869061ddadcc4863d0a2182541acae9a38", [:mix], [], "hexpm", "7af5c7e09fe1d40f76c8e4f9dd2be7cebd83909f31fee7cd0e9eadc567da8353"},
   "certifi": {:hex, :certifi, "2.9.0", "6f2a475689dd47f19fb74334859d460a2dc4e3252a3324bd2111b8f0429e7e21", [:rebar3], [], "hexpm", "266da46bdb06d6c6d35fde799bcb28d36d985d424ad7c08b5bb48f5b5cdd4641"},