diff --git a/packages/next/server/base-server.ts b/packages/next/server/base-server.ts
index a6da2bd95780..236f1fad44ff 100644
--- a/packages/next/server/base-server.ts
+++ b/packages/next/server/base-server.ts
@@ -1609,11 +1609,16 @@ export default abstract class Server<ServerOptions extends Options = Options> {
       }
 
       res.statusCode = 500
+
+      // if pages/500 is present we still need to trigger
+      // /_error `getInitialProps` to allow reporting error
+      if (await this.hasPage('/500')) {
+        ctx.query.__nextCustomErrorRender = '1'
+        await this.renderErrorToResponse(ctx, err)
+        delete ctx.query.__nextCustomErrorRender
+      }
+
       const isWrappedError = err instanceof WrappedBuildError
-      const response = await this.renderErrorToResponse(
-        ctx,
-        isWrappedError ? (err as WrappedBuildError).innerError : err
-      )
 
       if (!isWrappedError) {
         if (
@@ -1625,6 +1630,10 @@ export default abstract class Server<ServerOptions extends Options = Options> {
         }
         this.logError(getProperError(err))
       }
+      const response = await this.renderErrorToResponse(
+        ctx,
+        isWrappedError ? (err as WrappedBuildError).innerError : err
+      )
       return response
     }
 
@@ -1713,7 +1722,11 @@ export default abstract class Server<ServerOptions extends Options = Options> {
       }
       let statusPage = `/${res.statusCode}`
 
-      if (!result && STATIC_STATUS_PAGES.includes(statusPage)) {
+      if (
+        !ctx.query.__nextCustomErrorRender &&
+        !result &&
+        STATIC_STATUS_PAGES.includes(statusPage)
+      ) {
         // skip ensuring /500 in dev mode as it isn't used and the
         // dev overlay is used instead
         if (statusPage !== '/500' || !this.renderOpts.dev) {
diff --git a/packages/next/server/request-meta.ts b/packages/next/server/request-meta.ts
index 68ddb22a7280..39985a491848 100644
--- a/packages/next/server/request-meta.ts
+++ b/packages/next/server/request-meta.ts
@@ -63,6 +63,7 @@ type NextQueryMetadata = {
   __nextSsgPath?: string
   _nextBubbleNoFallback?: '1'
   __nextDataReq?: '1'
+  __nextCustomErrorRender?: '1'
 }
 
 export type NextParsedUrlQuery = ParsedUrlQuery &
diff --git a/test/production/custom-error-500/index.test.ts b/test/production/custom-error-500/index.test.ts
new file mode 100644
index 000000000000..2dba5785f3cf
--- /dev/null
+++ b/test/production/custom-error-500/index.test.ts
@@ -0,0 +1,77 @@
+import { createNext } from 'e2e-utils'
+import { NextInstance } from 'test/lib/next-modes/base'
+import { check, renderViaHTTP } from 'next-test-utils'
+
+describe('custom-error-500', () => {
+  let next: NextInstance
+
+  beforeAll(async () => {
+    next = await createNext({
+      files: {
+        'pages/index.js': `
+          export function getServerSideProps() {
+            throw new Error('custom error')
+          }
+          
+          export default function Page() {
+            return <p>index page</p>
+          }
+        `,
+        'pages/500.js': `
+          export default function Custom500() {
+            return (
+              <>
+                <p>pages/500</p>
+              </>
+            )
+          }
+        `,
+        'pages/_error.js': `
+          function Error({ hasError }) {
+            return (
+              <>
+                <p>/_error</p>
+              </>
+            )
+          }
+          
+          Error.getInitialProps = ({ err }) => {
+            console.log(\`called Error.getInitialProps \${!!err}\`)
+            return {
+              hasError: !!err
+            }
+          }
+          
+          export default Error
+        `,
+      },
+      dependencies: {},
+    })
+  })
+  afterAll(() => next.destroy())
+
+  it('should correctly use pages/500 and call Error.getInitialProps', async () => {
+    const html = await renderViaHTTP(next.url, '/')
+    expect(html).toContain('pages/500')
+
+    await check(() => next.cliOutput, /called Error\.getInitialProps true/)
+  })
+
+  it('should work correctly with pages/404 present', async () => {
+    await next.stop()
+    await next.patchFile(
+      'pages/404.js',
+      `
+      export default function Page() {
+        return <p>custom 404 page</p>
+      }
+    `
+    )
+    await next.start()
+
+    const html = await renderViaHTTP(next.url, '/')
+    expect(html).toContain('pages/500')
+
+    await check(() => next.cliOutput, /called Error\.getInitialProps true/)
+  })
+})