diff --git a/CHANGELOG.md b/CHANGELOG.md
index cf9c19e..c942741 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,8 @@
 # Changes
 
+* 2.6.next in progress
+  * Make SQL Server dialect auto-lift Boolean values to parameters since SQL Server has no `TRUE` / `FALSE` literals.
+
 * 2.6.1243 -- 2024-12-13
   * Address [#558](https://github.com/seancorfield/honeysql/issues/558) by adding `:patch-into` (and `patch-into` helper) for XTDB (but in core).
   * Address [#556](https://github.com/seancorfield/honeysql/issues/556) by adding an XTDB section to the documentation with examples.
diff --git a/src/honey/sql.cljc b/src/honey/sql.cljc
index 093c7dd..d1d9765 100644
--- a/src/honey/sql.cljc
+++ b/src/honey/sql.cljc
@@ -112,7 +112,8 @@
                 (assoc m k (assoc v :dialect k)))
               {}
               {:ansi      {:quote #(strop "\"" % "\"")}
-               :sqlserver {:quote #(strop "[" % "]")}
+               :sqlserver {:quote #(strop "[" % "]")
+                           :auto-lift-boolean true}
                :mysql     {:quote #(strop "`" % "`")
                            :clause-order-fn
                            #(add-clause-before % :set :where)}
@@ -2233,7 +2234,9 @@
                (into [(str "(" (join ", " sqls) ")")] params))))
 
          (boolean? expr)
-         [(upper-case (str expr))]
+         (if (:auto-lift-boolean *dialect*)
+           ["?" expr]
+           [(upper-case (str expr))])
 
          (nil? expr)
          ["NULL"]
diff --git a/test/honey/sql_test.cljc b/test/honey/sql_test.cljc
index 40a2fc0..8e697eb 100644
--- a/test/honey/sql_test.cljc
+++ b/test/honey/sql_test.cljc
@@ -22,6 +22,8 @@
          (sut/format-expr [:is :id nil])))
   (is (= ["id = TRUE"]
          (sut/format-expr [:= :id true])))
+  (is (= ["[id] = ?" true]
+         (sut/format [:= :id true] {:dialect :sqlserver})))
   (is (= ["id IS TRUE"]
          (sut/format-expr [:is :id true])))
   (is (= ["id <> TRUE"]