diff --git a/jOOQ/src/main/java/org/jooq/impl/DSL.java b/jOOQ/src/main/java/org/jooq/impl/DSL.java
index 156a9f0077..c149367a22 100644
--- a/jOOQ/src/main/java/org/jooq/impl/DSL.java
+++ b/jOOQ/src/main/java/org/jooq/impl/DSL.java
@@ -27270,6 +27270,32 @@ public class DSL {
 
 
 
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diff --git a/jOOQ/src/main/java/org/jooq/impl/Tools.java b/jOOQ/src/main/java/org/jooq/impl/Tools.java
index 3372a689f8..7e52f9a7bc 100644
--- a/jOOQ/src/main/java/org/jooq/impl/Tools.java
+++ b/jOOQ/src/main/java/org/jooq/impl/Tools.java
@@ -1210,6 +1210,7 @@ final class Tools {
     static final Set<SQLDialect>         NO_SUPPORT_TIMESTAMP_PRECISION             = SQLDialect.supportedBy(DERBY);
     static final Set<SQLDialect>         DEFAULT_TIMESTAMP_NOT_NULL                 = SQLDialect.supportedBy(MARIADB);
     static final Set<SQLDialect>         REQUIRES_PARENTHESISED_DEFAULT             = SQLDialect.supportedBy(SQLITE);
+    static final Set<SQLDialect>         REQUIRES_PARENTHESISED_DEFAULT_FOR_LOBS    = SQLDialect.supportedBy(MYSQL);
     static final Set<SQLDialect>         NO_SUPPORT_DEFAULT_DATETIME_LITERAL_PREFIX = SQLDialect.supportedBy(MARIADB, MYSQL);
 
 
@@ -5961,6 +5962,10 @@ final class Tools {
             if (REQUIRES_PARENTHESISED_DEFAULT.contains(ctx.dialect()))
                 ctx.sql('(').visit(v).sql(')');
 
+            // [#16853] MySQL LOB types can't have defaults. Except if we parenthesise them, then they can o_O
+            else if (REQUIRES_PARENTHESISED_DEFAULT_FOR_LOBS.contains(ctx.dialect()) && (type.isLob() || type.isJSON() || type.isSpatial()))
+                ctx.sql('(').visit(v).sql(')');
+
             // [#16498] Special cases where the standard datetime literal prefix needs to be omitted
             //          See: https://bugs.mysql.com/bug.php?id=114450
             else if (NO_SUPPORT_DEFAULT_DATETIME_LITERAL_PREFIX.contains(ctx.dialect()) && type.isDateTime())