diff --git a/core/server/services/redirects/validation.js b/core/server/services/redirects/validation.js
index 4975276935..98067da4f3 100644
--- a/core/server/services/redirects/validation.js
+++ b/core/server/services/redirects/validation.js
@@ -4,6 +4,7 @@ const errors = require('@tryghost/errors');
 
 const messages = {
     redirectsWrongFormat: 'Incorrect redirects file format.',
+    invalidRedirectsFromRegex: 'Incorrect RegEx in redirects file.',
     redirectsHelp: 'https://ghost.org/docs/themes/routing/#redirects'
 };
 /**
@@ -26,6 +27,17 @@ const validate = (redirects) => {
                 help: tpl(messages.redirectsHelp)
             });
         }
+
+        try {
+            // each 'from' property should be a valid RegExp string
+            new RegExp(redirect.from);
+        } catch (error) {
+            throw new errors.ValidationError({
+                message: tpl(messages.invalidRedirectsFromRegex),
+                context: redirect,
+                help: tpl(messages.redirectsHelp)
+            });
+        }
     });
 };
 
diff --git a/core/server/web/shared/middlewares/custom-redirects.js b/core/server/web/shared/middlewares/custom-redirects.js
index 866094ca3e..4679a7182f 100644
--- a/core/server/web/shared/middlewares/custom-redirects.js
+++ b/core/server/web/shared/middlewares/custom-redirects.js
@@ -96,11 +96,11 @@ _private.registerRoutes = (router, redirects) => {
 
 const loadRoutes = () => {
     try {
+        customRedirectsRouter = express.Router('redirects');
+
         const redirects = redirectsService.loadRedirectsFile();
         redirectsService.validate(redirects);
 
-        customRedirectsRouter = express.Router('redirects');
-
         _private.registerRoutes(customRedirectsRouter, redirects);
     } catch (err) {
         if (errors.utils.isIgnitionError(err)) {
diff --git a/test/unit/services/redirects/validation.test.js b/test/unit/services/redirects/validation.test.js
new file mode 100644
index 0000000000..88e3b8222a
--- /dev/null
+++ b/test/unit/services/redirects/validation.test.js
@@ -0,0 +1,44 @@
+const should = require('should');
+
+const {validate} = require('../../../../core/server/services/redirects/validation');
+
+describe('UNIT: custom redirects validation', function () {
+    it('passes validation for a valid redirects config', function () {
+        const config = [{
+            permanent: true,
+            from: '/test-params',
+            to: '/result?q=abc'
+        }];
+
+        validate(config);
+    });
+
+    it('throws for an invalid redirects config format missing from parameter', function () {
+        const config = [{
+            permanent: true,
+            to: '/'
+        }];
+
+        try {
+            validate(config);
+            should.fail('should have thrown');
+        } catch (err) {
+            err.message.should.equal('Incorrect redirects file format.');
+        }
+    });
+
+    it('throws for an invalid redirects config having invalid RegExp in from field', function () {
+        const config = [{
+            permanent: true,
+            from: '/invalid_regex/(/size/[a-zA-Z0-9_-.]*/[a-zA-Z0-9_-.]*/[0-9]*/[0-9]*/)([a-zA-Z0-9_-.]*)',
+            to: '/'
+        }];
+
+        try {
+            validate(config);
+            should.fail('should have thrown');
+        } catch (err) {
+            err.message.should.equal('Incorrect RegEx in redirects file.');
+        }
+    });
+});
diff --git a/test/unit/web/shared/middleware/custom-redirects.test.js b/test/unit/web/shared/middleware/custom-redirects.test.js
index 65d9a9bafa..00a3096462 100644
--- a/test/unit/web/shared/middleware/custom-redirects.test.js
+++ b/test/unit/web/shared/middleware/custom-redirects.test.js
@@ -2,10 +2,10 @@ const should = require('should');
 const sinon = require('sinon');
 const rewire = require('rewire');
 const express = require('express');
+const supertest = require('supertest');
 
 const customRedirects = rewire('../../../../../core/server/web/shared/middlewares/custom-redirects');
 const registerRoutes = customRedirects.__get__('_private.registerRoutes');
-const supertest = require('supertest');
 
 describe('UNIT: custom redirects', function () {
     let res;