diff --git a/sqlglot-integration-tests b/sqlglot-integration-tests
index 520efdb573..9816f9b42d 160000
--- a/sqlglot-integration-tests
+++ b/sqlglot-integration-tests
@@ -1 +1 @@
-Subproject commit 520efdb573b6da4d4aa5ea372bb3d49af6a3ddc6
+Subproject commit 9816f9b42dd90d60243a55b3ceae2f7f6db2c79e
diff --git a/sqlglot/expressions/functions.py b/sqlglot/expressions/functions.py
index e0442205b7..2d33343466 100644
--- a/sqlglot/expressions/functions.py
+++ b/sqlglot/expressions/functions.py
@@ -70,7 +70,7 @@ def is_type(self, *dtypes: DATA_TYPE) -> bool:
 
 
 class TryCast(Cast):
-    arg_types = {**Cast.arg_types, "requires_string": False}
+    arg_types = {**Cast.arg_types, "requires_string": False, "dialect_cast": False}
 
 
 class JSONCast(Cast):
diff --git a/sqlglot/generators/duckdb.py b/sqlglot/generators/duckdb.py
index 49a4d486b5..4d51ecc216 100644
--- a/sqlglot/generators/duckdb.py
+++ b/sqlglot/generators/duckdb.py
@@ -4326,6 +4326,28 @@ def round_sql(self, expression: exp.Round) -> str:
 
         return self.func(func, this, decimals, truncate)
 
+    def trycast_sql(self, expression: exp.TryCast) -> str:
+        if not expression.args.get("dialect_cast"):
+            return super().trycast_sql(expression)
+
+        src = expression.this
+        to = expression.to
+        to_type = to.this
+
+        if to_type == exp.DType.BOOLEAN:
+            return _to_boolean_sql(self, exp.ToBoolean(this=src, safe=True))
+        elif to_type in exp.DataType.TEXT_TYPES and to.expressions:
+            return self.sql(
+                exp.case()
+                .when(
+                    exp.LTE(this=exp.func("LENGTH", src), expression=to.expressions[0].this),
+                    exp.cast(src, "TEXT"),
+                )
+                .else_(exp.Null())
+            )
+
+        return super().trycast_sql(expression)
+
     def strtok_sql(self, expression: exp.Strtok) -> str:
         string_arg = expression.this
         delimiter_arg = expression.args.get("delimiter")
diff --git a/sqlglot/parser.py b/sqlglot/parser.py
index 73e0520b56..262f2f698b 100644
--- a/sqlglot/parser.py
+++ b/sqlglot/parser.py
@@ -9928,6 +9928,10 @@ def build_cast(self, strict: bool, **kwargs) -> exp.Cast:
 
         if exp_class == exp.TryCast:
             kwargs["requires_string"] = self.dialect.TRY_CAST_REQUIRES_STRING
+            if self.dialect.TRY_CAST_REQUIRES_STRING and (to := kwargs.get("to")):
+                kwargs["dialect_cast"] = to.this == exp.DataType.Type.BOOLEAN or (
+                    to.this in exp.DataType.TEXT_TYPES and bool(to.expressions)
+                )
 
         return self.expression(exp_class(**kwargs))