diff --git a/api/src/database/migrations/20201105B-change-webhook-url-type.ts b/api/src/database/migrations/20201105B-change-webhook-url-type.ts
index cc274907ae..d1ad118cc5 100644
--- a/api/src/database/migrations/20201105B-change-webhook-url-type.ts
+++ b/api/src/database/migrations/20201105B-change-webhook-url-type.ts
@@ -1,12 +1,31 @@
 import { Knex } from 'knex';
+import env from '../../env';
+
+async function oracleAlterUrl(knex: Knex, type: string): Promise<void> {
+	await knex.raw('ALTER TABLE "directus_webhooks" ADD "url__temp" ?', [knex.raw(type)]);
+	await knex.raw('UPDATE "directus_webhooks" SET "url__temp"="url"');
+	await knex.raw('ALTER TABLE "directus_webhooks" DROP COLUMN "url"');
+	await knex.raw('ALTER TABLE "directus_webhooks" RENAME COLUMN "url__temp" TO "url"');
+	await knex.raw('ALTER TABLE "directus_webhooks" MODIFY "url" NOT NULL');
+}
 
 export async function up(knex: Knex): Promise<void> {
+	if (env.DB_CLIENT === 'oracledb') {
+		await oracleAlterUrl(knex, 'CLOB');
+		return;
+	}
+
 	await knex.schema.alterTable('directus_webhooks', (table) => {
 		table.text('url').alter();
 	});
 }
 
 export async function down(knex: Knex): Promise<void> {
+	if (env.DB_CLIENT === 'oracledb') {
+		await oracleAlterUrl(knex, 'VARCHAR2(255)');
+		return;
+	}
+
 	await knex.schema.alterTable('directus_webhooks', (table) => {
 		table.string('url').alter();
 	});
diff --git a/api/src/database/migrations/20210312A-webhooks-collections-text.ts b/api/src/database/migrations/20210312A-webhooks-collections-text.ts
index 43b31ab628..09cd50b5c1 100644
--- a/api/src/database/migrations/20210312A-webhooks-collections-text.ts
+++ b/api/src/database/migrations/20210312A-webhooks-collections-text.ts
@@ -1,12 +1,31 @@
 import { Knex } from 'knex';
+import env from '../../env';
+
+async function oracleAlterCollections(knex: Knex, type: string): Promise<void> {
+	await knex.raw('ALTER TABLE "directus_webhooks" ADD "collections__temp" ?', [knex.raw(type)]);
+	await knex.raw('UPDATE "directus_webhooks" SET "collections__temp"="collections"');
+	await knex.raw('ALTER TABLE "directus_webhooks" DROP COLUMN "collections"');
+	await knex.raw('ALTER TABLE "directus_webhooks" RENAME COLUMN "collections__temp" TO "collections"');
+	await knex.raw('ALTER TABLE "directus_webhooks" MODIFY "collections" NOT NULL');
+}
 
 export async function up(knex: Knex): Promise<void> {
+	if (env.DB_CLIENT === 'oracledb') {
+		await oracleAlterCollections(knex, 'CLOB');
+		return;
+	}
+
 	await knex.schema.alterTable('directus_webhooks', (table) => {
 		table.text('collections').alter();
 	});
 }
 
 export async function down(knex: Knex): Promise<void> {
+	if (env.DB_CLIENT === 'oracledb') {
+		await oracleAlterCollections(knex, 'VARCHAR2(255)');
+		return;
+	}
+
 	await knex.schema.alterTable('directus_webhooks', (table) => {
 		table.string('collections').alter();
 	});