diff --git a/packages/backend/src/open_payments/wallet_address/service.test.ts b/packages/backend/src/open_payments/wallet_address/service.test.ts
index 910d00bb39..e363e111a9 100644
--- a/packages/backend/src/open_payments/wallet_address/service.test.ts
+++ b/packages/backend/src/open_payments/wallet_address/service.test.ts
@@ -59,7 +59,7 @@ describe('Open Payments Wallet Address Service', (): void => {
     await appContainer.shutdown()
   })
 
-  describe('Create or Get Wallet Address3', (): void => {
+  describe('Create or Get Wallet Address', (): void => {
     let tenantId: string
     let options: CreateOptions
 
@@ -606,6 +606,56 @@ describe('Open Payments Wallet Address Service', (): void => {
         )
       )
 
+      test(
+        'creates wallet address not found event for tenant with matching prefix',
+        withConfigOverride(
+          () => config,
+          { walletAddressLookupTimeoutMs: 0 },
+          async (): Promise<void> => {
+            const walletAddressUrl = `https://${faker.internet.domainName()}/.well-known/pay`
+            const tenant = await createTenant(deps)
+            await createTenantSettings(deps, {
+              tenantId: tenant.id,
+              setting: [
+                {
+                  key: TenantSettingKeys.WALLET_ADDRESS_URL.name,
+                  value: `${walletAddressUrl}/${uuid()}`
+                }
+              ]
+            })
+
+            await expect(
+              walletAddressService.getOrPollByUrl(walletAddressUrl)
+            ).resolves.toBeUndefined()
+
+            const walletAddressNotFoundEvents = await WalletAddressEvent.query(
+              knex
+            )
+              .where({
+                type: WalletAddressEventType.WalletAddressNotFound
+              })
+              .withGraphFetched('webhooks')
+
+            expect(walletAddressNotFoundEvents).toHaveLength(1)
+            expect(walletAddressNotFoundEvents[0].webhooks).toHaveLength(2)
+            expect(walletAddressNotFoundEvents[0]).toMatchObject({
+              data: { walletAddressUrl },
+              webhooks: expect.arrayContaining([
+                expect.objectContaining({
+                  recipientTenantId: tenant.id,
+                  eventId: walletAddressNotFoundEvents[0].id,
+                  processAt: expect.any(Date)
+                }),
+                expect.objectContaining({
+                  recipientTenantId: config.operatorTenantId,
+                  eventId: walletAddressNotFoundEvents[0].id,
+                  processAt: expect.any(Date)
+                })
+              ])
+            })
+          }
+        )
+      )
       test(
         'polls for wallet address',
         withConfigOverride(
diff --git a/packages/backend/src/open_payments/wallet_address/service.ts b/packages/backend/src/open_payments/wallet_address/service.ts
index 86ae1d2b62..79c9669e63 100644
--- a/packages/backend/src/open_payments/wallet_address/service.ts
+++ b/packages/backend/src/open_payments/wallet_address/service.ts
@@ -379,13 +379,25 @@ async function getOrPollByUrl(
   const existingWalletAddress = await getWalletAddressByUrl(deps, url)
   if (existingWalletAddress) return existingWalletAddress
 
+  let containsOperatorTenant = false
+  const webhookRecipients = (
+    await deps.tenantSettingService.getSettingsByPrefix(url)
+  ).map((tenantSetting) => {
+    if (tenantSetting.tenantId === deps.config.operatorTenantId)
+      containsOperatorTenant = true
+    return { recipientTenantId: tenantSetting.tenantId }
+  })
+
+  if (!containsOperatorTenant)
+    webhookRecipients.push({ recipientTenantId: deps.config.operatorTenantId })
+
   await WalletAddressEvent.query(deps.knex).insertGraph({
     type: WalletAddressEventType.WalletAddressNotFound,
     data: {
       walletAddressUrl: url
     },
     tenantId: deps.config.operatorTenantId,
-    webhooks: [{ recipientTenantId: deps.config.operatorTenantId }]
+    webhooks: webhookRecipients
   })
 
   deps.logger.debug(
diff --git a/packages/backend/src/tenants/settings/service.test.ts b/packages/backend/src/tenants/settings/service.test.ts
index f0631b14fc..5ceeb2556b 100644
--- a/packages/backend/src/tenants/settings/service.test.ts
+++ b/packages/backend/src/tenants/settings/service.test.ts
@@ -9,7 +9,7 @@ import { Tenant } from '../model'
 import { TenantService } from '../service'
 import { faker } from '@faker-js/faker'
 import { exchangeRatesSetting, randomSetting } from '../../tests/tenantSettings'
-import { TenantSetting } from './model'
+import { TenantSetting, TenantSettingKeys } from './model'
 import {
   CreateOptions,
   GetOptions,
@@ -17,6 +17,8 @@ import {
   UpdateOptions
 } from './service'
 import { AuthServiceClient } from '../../auth-service-client/client'
+import { v4 as uuid } from 'uuid'
+import { createTenant } from '../../tests/tenant'
 
 describe('TenantSetting Service', (): void => {
   let deps: IocContract<AppServices>
@@ -371,4 +373,67 @@ describe('TenantSetting Service', (): void => {
       expect(result).toEqual([])
     })
   })
+
+  describe('get settings by value', (): void => {
+    test('can get settings by wallet address prefix setting', async (): Promise<void> => {
+      const secondTenant = await createTenant(deps)
+      const baseUrl = `https://${faker.internet.domainName()}/${uuid()}`
+      const settings = (
+        await Promise.all([
+          tenantSettingService.create({
+            tenantId: tenant.id,
+            setting: [
+              {
+                key: TenantSettingKeys.WALLET_ADDRESS_URL.name,
+                value: `${baseUrl}/${uuid()}`
+              }
+            ]
+          }),
+          tenantSettingService.create({
+            tenantId: secondTenant.id,
+            setting: [
+              {
+                key: TenantSettingKeys.WALLET_ADDRESS_URL.name,
+                value: `${baseUrl}/${uuid()}`
+              }
+            ]
+          })
+        ])
+      ).flat()
+
+      const retrievedSettings =
+        await tenantSettingService.getSettingsByPrefix(baseUrl)
+      expect(retrievedSettings).toEqual(settings)
+    })
+
+    test('does not retrieve tenants if no wallet address prefix matches', async (): Promise<void> => {
+      const secondTenant = await createTenant(deps)
+      const baseUrl = `https://${faker.internet.domainName()}/${uuid()}`
+      await Promise.all([
+        tenantSettingService.create({
+          tenantId: tenant.id,
+          setting: [
+            {
+              key: TenantSettingKeys.WALLET_ADDRESS_URL.name,
+              value: `${baseUrl}/${uuid()}`
+            }
+          ]
+        }),
+        tenantSettingService.create({
+          tenantId: secondTenant.id,
+          setting: [
+            {
+              key: TenantSettingKeys.WALLET_ADDRESS_URL.name,
+              value: `${baseUrl}/${uuid()}`
+            }
+          ]
+        })
+      ])
+
+      const retrievedSettings = await tenantSettingService.getSettingsByPrefix(
+        faker.internet.url()
+      )
+      expect(retrievedSettings).toHaveLength(0)
+    })
+  })
 })
diff --git a/packages/backend/src/tenants/settings/service.ts b/packages/backend/src/tenants/settings/service.ts
index 5623928bf1..9989f814a1 100644
--- a/packages/backend/src/tenants/settings/service.ts
+++ b/packages/backend/src/tenants/settings/service.ts
@@ -43,6 +43,7 @@ export interface TenantSettingService {
     pagination?: Pagination,
     sortOrder?: SortOrder
   ) => Promise<TenantSetting[]>
+  getSettingsByPrefix: (prefix: string) => Promise<TenantSetting[]>
 }
 
 export interface ServiceDependencies extends BaseService {
@@ -68,7 +69,9 @@ export async function createTenantSettingService(
       tenantId: string,
       pagination?: Pagination,
       sortOrder?: SortOrder
-    ) => getTenantSettingPageForTenant(deps, tenantId, pagination, sortOrder)
+    ) => getTenantSettingPageForTenant(deps, tenantId, pagination, sortOrder),
+    getSettingsByPrefix: (prefix: string) =>
+      getWalletAddressSettingsByPrefix(deps, prefix)
   }
 }
 
@@ -147,3 +150,14 @@ async function getTenantSettingPageForTenant(
     .andWhere('tenantId', tenantId)
     .getPage(pagination, sortOrder)
 }
+
+async function getWalletAddressSettingsByPrefix(
+  deps: ServiceDependencies,
+  prefix: string
+): Promise<TenantSetting[]> {
+  return await TenantSetting.query(deps.knex)
+    .whereILike('value', `${prefix}%`)
+    .andWhere({
+      key: TenantSettingKeys.WALLET_ADDRESS_URL.name
+    })
+}