diff --git a/src/server/routes/index.ts b/src/server/routes/index.ts
index 55b85618..1532c4ea 100644
--- a/src/server/routes/index.ts
+++ b/src/server/routes/index.ts
@@ -26,24 +26,39 @@ import { PG_CONNECTION, CRYPTO_KEY } from '../constants.js'
 export default async (fastify: FastifyInstance) => {
   // Adds a "pg" object to the request if it doesn't exist
   fastify.addHook('onRequest', (request, _reply, done) => {
-    // Node converts headers to lowercase
-    const encryptedHeader = request.headers['x-connection-encrypted']?.toString()
-    if (encryptedHeader) {
+    try {
+      // Node converts headers to lowercase
+      const encryptedHeader = request.headers['x-connection-encrypted']?.toString()
+      if (encryptedHeader) {
+        try {
+          request.headers.pg = CryptoJS.AES.decrypt(encryptedHeader, CRYPTO_KEY)
+            .toString(CryptoJS.enc.Utf8)
+            .trim()
+        } catch (e: any) {
+          request.log.warn({
+            message: 'failed to parse encrypted connstring',
+            error: e.toString(),
+          })
+          throw new Error('failed to process upstream connection details')
+        }
+      } else {
+        request.headers.pg = PG_CONNECTION
+      }
+      if (!request.headers.pg) {
+        request.log.error({ message: 'failed to get connection string' })
+        throw new Error('failed to get upstream connection details')
+      }
+      // Ensure the resulting connection string is a valid URL
       try {
-        request.headers.pg = CryptoJS.AES.decrypt(encryptedHeader, CRYPTO_KEY).toString(
-          CryptoJS.enc.Utf8
-        )
-      } catch (e: any) {
-        request.log.warn({
-          message: 'failed to parse encrypted connstring',
-          error: e.toString(),
-        })
+        new URL(request.headers.pg)
+      } catch (error) {
+        request.log.error({ message: 'pg connection string is invalid url' })
         throw new Error('failed to process upstream connection details')
       }
-    } else {
-      request.headers.pg = PG_CONNECTION
+      return done()
+    } catch (err) {
+      return done(err as Error)
     }
-    done()
   })
 
   fastify.register(ColumnPrivilegesRoute, { prefix: '/column-privileges' })
diff --git a/test/server/ssl.ts b/test/server/ssl.ts
index 05944dac..5b6cc83b 100644
--- a/test/server/ssl.ts
+++ b/test/server/ssl.ts
@@ -72,3 +72,57 @@ test('query with ssl with root cert', async () => {
 
   DEFAULT_POOL_CONFIG.ssl = defaultSsl
 })
+
+test('query with invalid space empty encrypted connection string', async () => {
+  const res = await app.inject({
+    method: 'POST',
+    path: '/query',
+    headers: {
+      'x-connection-encrypted': CryptoJS.AES.encrypt(` `, CRYPTO_KEY).toString(),
+    },
+    payload: { query: 'select 1;' },
+  })
+  expect(res.statusCode).toBe(500)
+  expect(res.json()).toMatchInlineSnapshot(`
+    {
+      "error": "failed to get upstream connection details",
+    }
+  `)
+})
+
+test('query with invalid empty encrypted connection string', async () => {
+  const res = await app.inject({
+    method: 'POST',
+    path: '/query',
+    headers: {
+      'x-connection-encrypted': CryptoJS.AES.encrypt(``, CRYPTO_KEY).toString(),
+    },
+    payload: { query: 'select 1;' },
+  })
+  expect(res.statusCode).toBe(500)
+  expect(res.json()).toMatchInlineSnapshot(`
+    {
+      "error": "failed to get upstream connection details",
+    }
+  `)
+})
+
+test('query with missing host connection string encrypted connection string', async () => {
+  const res = await app.inject({
+    method: 'POST',
+    path: '/query',
+    headers: {
+      'x-connection-encrypted': CryptoJS.AES.encrypt(
+        `postgres://name:password@:5432/postgres?sslmode=prefer`,
+        CRYPTO_KEY
+      ).toString(),
+    },
+    payload: { query: 'select 1;' },
+  })
+  expect(res.statusCode).toBe(500)
+  expect(res.json()).toMatchInlineSnapshot(`
+    {
+      "error": "failed to process upstream connection details",
+    }
+  `)
+})