diff --git a/jOOQ/src/main/java/org/jooq/impl/JSONArray.java b/jOOQ/src/main/java/org/jooq/impl/JSONArray.java
index 490d29bb38..879da26648 100644
--- a/jOOQ/src/main/java/org/jooq/impl/JSONArray.java
+++ b/jOOQ/src/main/java/org/jooq/impl/JSONArray.java
@@ -43,6 +43,7 @@ import static org.jooq.impl.DSL.row;
 import static org.jooq.impl.DSL.select;
 import static org.jooq.impl.DSL.unquotedName;
 import static org.jooq.impl.DSL.values;
+import static org.jooq.impl.JSONEntryImpl.jsonCastMapper;
 import static org.jooq.impl.JSONNull.JSONNullType.ABSENT_ON_NULL;
 import static org.jooq.impl.JSONNull.JSONNullType.NULL_ON_NULL;
 import static org.jooq.impl.Keywords.K_JSON_ARRAY;
@@ -115,8 +116,10 @@ final class JSONArray<J> extends AbstractField<J> implements JSONArrayNullStep<J
             case POSTGRES:
                 if (nullType == ABSENT_ON_NULL) {
                     Row1[] rows = new Row1[args.size()];
+
                     for (int i = 0; i < rows.length; i++)
                         rows[i] = row(args.get(i));
+
                     Table<?> t = values(rows).as("t", "a");
                     Field<?> a = t.field("a");
                     ctx.visit(DSL.field(select(jsonArrayAgg(a)).from(t).where(a.isNotNull())));
@@ -136,7 +139,7 @@ final class JSONArray<J> extends AbstractField<J> implements JSONArrayNullStep<J
                 else
                     jsonNull = new JSONNull(nullType);
 
-                ctx.visit(K_JSON_ARRAY).sql('(').visit(wrap(args, jsonNull).separator("")).sql(')');
+                ctx.visit(K_JSON_ARRAY).sql('(').visit(wrap(wrap(args).map(jsonCastMapper(ctx)), jsonNull).separator("")).sql(')');
                 break;
             }
         }
diff --git a/jOOQ/src/main/java/org/jooq/impl/JSONArrayAgg.java b/jOOQ/src/main/java/org/jooq/impl/JSONArrayAgg.java
index ba86745552..40e257df9e 100644
--- a/jOOQ/src/main/java/org/jooq/impl/JSONArrayAgg.java
+++ b/jOOQ/src/main/java/org/jooq/impl/JSONArrayAgg.java
@@ -43,6 +43,7 @@ import static org.jooq.SQLDialect.MYSQL;
 import static org.jooq.impl.DSL.function;
 import static org.jooq.impl.DSL.groupConcat;
 import static org.jooq.impl.DSL.inline;
+import static org.jooq.impl.JSONEntryImpl.jsonCast;
 import static org.jooq.impl.JSONNull.JSONNullType.ABSENT_ON_NULL;
 import static org.jooq.impl.JSONNull.JSONNullType.NULL_ON_NULL;
 import static org.jooq.impl.Names.N_JSONB_AGG;
@@ -157,7 +158,7 @@ implements JSONArrayAggOrderByStep<J> {
 
     private final void acceptStandard(Context<?> ctx) {
         ctx.visit(N_JSON_ARRAYAGG).sql('(');
-        ctx.visit(arguments.get(0));
+        ctx.visit(jsonCast(ctx, arguments.get(0)));
         acceptOrderBy(ctx);
 
         JSONNull jsonNull = new JSONNull(nullType);
diff --git a/jOOQ/src/main/java/org/jooq/impl/JSONEntryImpl.java b/jOOQ/src/main/java/org/jooq/impl/JSONEntryImpl.java
index b5f969e361..25c828bfea 100644
--- a/jOOQ/src/main/java/org/jooq/impl/JSONEntryImpl.java
+++ b/jOOQ/src/main/java/org/jooq/impl/JSONEntryImpl.java
@@ -42,8 +42,12 @@ import static org.jooq.impl.Keywords.K_FORMAT;
 import static org.jooq.impl.Keywords.K_JSON;
 import static org.jooq.impl.Keywords.K_KEY;
 import static org.jooq.impl.Keywords.K_VALUE;
+import static org.jooq.impl.SQLDataType.VARCHAR;
+
+import java.util.UUID;
 
 import org.jooq.Context;
+import org.jooq.DataType;
 import org.jooq.Field;
 import org.jooq.JSONEntry;
 
@@ -106,8 +110,32 @@ final class JSONEntryImpl<T> extends AbstractQueryPart implements JSONEntry<T> {
                 break;
 
             default:
-                ctx.visit(K_KEY).sql(' ').visit(key).sql(' ').visit(K_VALUE).sql(' ').visit(value);
+                ctx.visit(K_KEY).sql(' ').visit(key).sql(' ').visit(K_VALUE).sql(' ').visit(jsonCast(ctx, value));
                 break;
         }
     }
+
+    static final F1<Field<?>, Field<?>> jsonCastMapper(final Context<?> ctx) {
+        return new F1<Field<?>, Field<?>>() {
+            @Override
+            public Field<?> apply(Field<?> field) {
+                return jsonCast(ctx, field);
+            }
+        };
+    }
+
+    static final Field<?> jsonCast(Context<?> ctx, Field<?> field) {
+        switch (ctx.family()) {
+
+            // [#10769] Some dialects don't support auto conversions from X to JSON
+            case H2: {
+                DataType<?> type = field.getDataType();
+
+                if (type.getType() == UUID.class)
+                    return field.cast(VARCHAR(36));
+            }
+        }
+
+        return field;
+    }
 }
diff --git a/jOOQ/src/main/java/org/jooq/impl/JSONObject.java b/jOOQ/src/main/java/org/jooq/impl/JSONObject.java
index d44ecc05cf..f67ec001d7 100644
--- a/jOOQ/src/main/java/org/jooq/impl/JSONObject.java
+++ b/jOOQ/src/main/java/org/jooq/impl/JSONObject.java
@@ -54,8 +54,10 @@ import static org.jooq.impl.Names.N_JSON_MERGE;
 import static org.jooq.impl.Names.N_JSON_OBJECT;
 import static org.jooq.impl.Names.N_T;
 import static org.jooq.impl.QueryPartListView.wrap;
+import static org.jooq.impl.SQLDataType.VARCHAR;
 
 import java.util.Collection;
+import java.util.UUID;
 
 import org.jooq.Context;
 import org.jooq.DataType;