diff --git a/packages/backend-common/src/service/lib/ServiceBuilderImpl.ts b/packages/backend-common/src/service/lib/ServiceBuilderImpl.ts
index 46bf23beef..9c5ac20fa3 100644
--- a/packages/backend-common/src/service/lib/ServiceBuilderImpl.ts
+++ b/packages/backend-common/src/service/lib/ServiceBuilderImpl.ts
@@ -145,7 +145,7 @@ export class ServiceBuilderImpl implements ServiceBuilder {
     return this;
   }
 
-  start(): Promise<http.Server> {
+  async start(): Promise<http.Server> {
     const app = express();
     const {
       port,
@@ -168,16 +168,16 @@ export class ServiceBuilderImpl implements ServiceBuilder {
     app.use(notFoundHandler());
     app.use(errorHandler());
 
+    const server: http.Server = httpsSettings
+      ? await createHttpsServer(app, httpsSettings, logger)
+      : createHttpServer(app, logger);
+
     return new Promise((resolve, reject) => {
       app.on('error', e => {
         logger.error(`Failed to start up on port ${port}, ${e}`);
         reject(e);
       });
 
-      const server: http.Server = httpsSettings
-        ? createHttpsServer(app, httpsSettings, logger)
-        : createHttpServer(app, logger);
-
       const stoppableServer = stoppable(
         server.listen(port, host, () => {
           logger.info(`Listening on ${host}:${port}`);
diff --git a/packages/backend-common/src/service/lib/hostFactory.ts b/packages/backend-common/src/service/lib/hostFactory.ts
index f190b847b6..656f160c31 100644
--- a/packages/backend-common/src/service/lib/hostFactory.ts
+++ b/packages/backend-common/src/service/lib/hostFactory.ts
@@ -13,11 +13,16 @@
  * See the License for the specific language governing permissions and
  * limitations under the License.
  */
+
+import fs from 'fs-extra';
+import { resolve as resolvePath, dirname } from 'path';
 import express from 'express';
 import * as http from 'http';
 import * as https from 'https';
 import { Logger } from 'winston';
-import { HttpsSettings } from './config';
+import { CertificateSigningOptions, HttpsSettings } from './config';
+
+const ALMOST_MONTH_IN_MS = 25 * 24 * 60 * 60 * 1000;
 
 /**
  * Creates a Http server instance based on an Express application.
@@ -45,100 +50,152 @@ export function createHttpServer(
  * @returns A Https server instance
  *
  */
-export function createHttpsServer(
+export async function createHttpsServer(
   app: express.Express,
   httpsSettings: HttpsSettings,
   logger?: Logger,
-): http.Server {
+): Promise<http.Server> {
   logger?.info('Initializing https server');
 
-  const credentials: { key: string; cert: string } = {
-    key: '',
-    cert: '',
-  };
+  let credentials: { key: string | Buffer; cert: string | Buffer };
 
   const signingOptions: any = httpsSettings?.certificate;
 
+  // TODO(Rugvip): remove support for generated certificate params and make this a more straightforward check
   if (signingOptions?.attributes) {
-    logger?.info('Generating self-signed certificate with attributes');
-    if (signingOptions?.algorithm) {
-      logger?.warn(
-        'Certificate generation configuration with parameters in backend.https.certificate is deprecated, set backend.https = true instead',
-      );
-    }
-
-    const certificateAttributes: Array<any> = Object.entries(
-      signingOptions.attributes,
-    ).map(([name, value]) => ({ name, value }));
-
-    const signatures = require('selfsigned').generate(certificateAttributes, {
-      algorithm: signingOptions?.algorithm || 'sha256',
-      keySize: signingOptions?.size || 2048,
-      days: signingOptions?.days || 30,
-      extensions: [
-        {
-          name: 'keyUsage',
-          keyCertSign: true,
-          digitalSignature: true,
-          nonRepudiation: true,
-          keyEncipherment: true,
-          dataEncipherment: true,
-        },
-        {
-          name: 'extKeyUsage',
-          serverAuth: true,
-          clientAuth: true,
-          codeSigning: true,
-          timeStamping: true,
-        },
-        {
-          name: 'subjectAltName',
-          altNames: [
-            {
-              type: 2, // DNS
-              value: 'localhost',
-            },
-            {
-              type: 2,
-              value: 'localhost.localdomain',
-            },
-            {
-              type: 2,
-              value: '[::1]',
-            },
-            {
-              type: 7, // IP
-              ip: '127.0.0.1',
-            },
-            {
-              type: 7,
-              ip: 'fe80::1',
-            },
-            ...(signingOptions.attributes.commonName
-              ? [
-                  {
-                    type: 2, // DNS
-                    value: signingOptions.attributes.commonName,
-                  },
-                ]
-              : []),
-          ],
-        },
-      ],
-    });
-
-    credentials.key = signatures.private;
-    credentials.cert = signatures.cert;
+    credentials = await getGeneratedCertificate(signingOptions, logger);
   } else {
     logger?.info('Loading certificate from config');
 
-    credentials.key = signingOptions?.key;
-    credentials.cert = signingOptions?.cert;
+    credentials = {
+      key: signingOptions?.key,
+      cert: signingOptions?.cert,
+    };
   }
 
-  if (credentials.key === '' || credentials.cert === '') {
-    throw new Error('Invalid credentials');
+  if (!credentials.key || !credentials.cert) {
+    throw new Error('Invalid HTTPS credentials');
   }
 
   return https.createServer(credentials, app) as http.Server;
 }
+
+async function getGeneratedCertificate(
+  options: CertificateSigningOptions,
+  logger?: Logger,
+) {
+  if (options?.algorithm) {
+    logger?.warn(
+      'Certificate generation configuration with parameters in backend.https.certificate is deprecated, set backend.https = true instead',
+    );
+  }
+
+  const hasModules = await fs.pathExists('node_modules');
+  let certPath;
+  if (hasModules) {
+    certPath = resolvePath(
+      'node_modules/.cache/backstage-backend/dev-cert.pem',
+    );
+    await fs.ensureDir(dirname(certPath));
+  } else {
+    certPath = resolvePath('.dev-cert.pem');
+  }
+
+  let cert = undefined;
+  if (await fs.pathExists(certPath)) {
+    const stat = await fs.stat(certPath);
+    const ageMs = Date.now() - stat.ctimeMs;
+    if (stat.isFile() && ageMs < ALMOST_MONTH_IN_MS) {
+      cert = await fs.readFile(certPath);
+    }
+  }
+
+  if (cert) {
+    logger?.info('Using existing self-signed certificate');
+    return {
+      key: cert,
+      cert: cert,
+    };
+  }
+
+  logger?.info('Generating new self-signed certificate');
+  const newCert = await createCertificate(options);
+  await fs.writeFile(certPath, newCert.cert + newCert.key, 'utf8');
+  return newCert;
+}
+
+async function createCertificate(options: CertificateSigningOptions) {
+  const attributes: Array<any> = Object.entries(
+    options.attributes,
+  ).map(([name, value]) => ({ name, value }));
+
+  const params = {
+    algorithm: options?.algorithm || 'sha256',
+    keySize: options?.size || 2048,
+    days: options?.days || 30,
+    extensions: [
+      {
+        name: 'keyUsage',
+        keyCertSign: true,
+        digitalSignature: true,
+        nonRepudiation: true,
+        keyEncipherment: true,
+        dataEncipherment: true,
+      },
+      {
+        name: 'extKeyUsage',
+        serverAuth: true,
+        clientAuth: true,
+        codeSigning: true,
+        timeStamping: true,
+      },
+      {
+        name: 'subjectAltName',
+        altNames: [
+          {
+            type: 2, // DNS
+            value: 'localhost',
+          },
+          {
+            type: 2,
+            value: 'localhost.localdomain',
+          },
+          {
+            type: 2,
+            value: '[::1]',
+          },
+          {
+            type: 7, // IP
+            ip: '127.0.0.1',
+          },
+          {
+            type: 7,
+            ip: 'fe80::1',
+          },
+          ...(options.attributes.commonName
+            ? [
+                {
+                  type: 2, // DNS
+                  value: options.attributes.commonName,
+                },
+              ]
+            : []),
+        ],
+      },
+    ],
+  };
+
+  return new Promise<{ key: string; cert: string }>((resolve, reject) =>
+    require('selfsigned').generate(
+      attributes,
+      params,
+      (err: Error, bundle: { private: string; cert: string }) => {
+        if (err) {
+          reject(err);
+        } else {
+          resolve({ key: bundle.private, cert: bundle.cert });
+        }
+      },
+    ),
+  );
+}