diff --git a/lib/configuration/validateConfig.js b/lib/configuration/validateConfig.js
index ff0ea86a9..5b872d638 100644
--- a/lib/configuration/validateConfig.js
+++ b/lib/configuration/validateConfig.js
@@ -1,28 +1,48 @@
-/**
- * TODO Account for option aliases (i.e. "l", "q").
- * Enforce strict rules not to be able to coerce removed options, only the deprecated ones.
- */
-const deprecatedOptions = {
-  c: 'DEPRECATED: The `c` configuration option is deprecated. Plese use `color` instead.',
-  data: 'DEPRECATED: The `data` configuration option is deprecated '
+const deprecatedOptions = [
+  {
+    options: ['c'],
+    message: 'DEPRECATED: The -c configuration option is deprecated. Plese use --color instead.',
+  },
+  {
+    options: ['data'],
+    message: 'DEPRECATED: The --data configuration option is deprecated '
     + 'in favor of `apiDescriptions`, please see https://dredd.org',
-  blueprintPath: 'DEPRECATED: The `blueprintPath` configuration option is deprecated, '
-    + 'please use `path` instead.',
-  level: 'DEPRECATED: The `level` configuration option is deprecated. Please use `loglevel` instead.',
-};
+  },
+  {
+    options: ['blueprintPath'],
+    message: 'DEPRECATED: The --blueprintPath configuration option is deprecated, '
+    + 'please use --path instead.',
+  },
+  {
+    options: ['level'],
+    message: 'DEPRECATED: The --level configuration option is deprecated. Please use --loglevel instead.',
+  },
+];
 
-const unsupportedOptions = {
-  timestamp: 'REMOVED: The `timestamp` configuration option is removed. Please use `--loglevel=debug` instead.',
-  silent: 'REMOVED: The `silent` configuration option is removed. Please use `--loglevel=silent` instead.',
-  sandbox: 'REMOVED: Dredd does not support sandboxed JS hooks anymore, use standard JS hooks instead.',
-  hooksData: 'REMOVED: Dredd does not support sandboxed JS hooks anymore, use standard JS hooks instead.',
-};
+const unsupportedOptions = [
+  {
+    options: ['timestamp', 't'],
+    message: 'REMOVED: The --timestamp/-t configuration option is no longer supported. Please use --loglevel=debug instead.',
+  },
+  {
+    options: ['silent', 'q'],
+    message: 'REMOVED: The --silent/-q configuration option is no longer supported. Please use --loglevel=silent instead.',
+  },
+  {
+    options: ['sandbox', 'b'],
+    message: 'REMOVED: Dredd does not support sandboxed JS hooks anymore, use standard JS hooks instead.',
+  },
+  {
+    options: ['hooksData'],
+    message: 'REMOVED: Dredd does not support sandboxed JS hooks anymore, use standard JS hooks instead.',
+  },
+];
 
-function flushMessages(options, config) {
-  return Object.keys(options).reduce((messages, optionName) => (config[optionName]
-    ? messages.concat(options[optionName])
-    : messages
-  ), []);
+function flushMessages(rules, config) {
+  return Object.keys(config).reduce((messages, configKey) => {
+    const warning = rules.find(rule => rule.options.includes(configKey));
+    return warning ? messages.concat(warning.message) : messages;
+  }, []);
 }
 
 /**
diff --git a/test/unit/configuration-test.js b/test/unit/configuration-test.js
index 6497fe7c5..3a69668fe 100644
--- a/test/unit/configuration-test.js
+++ b/test/unit/configuration-test.js
@@ -322,13 +322,12 @@ describe('configuration', () => {
     });
   });
 
-  describe('with --timestamp/-t set', () => {
-    const config = { timestamp: true, t: true };
+  describe('with --timestamp set', () => {
+    const config = { timestamp: true };
     const normalizedConfig = normalizeConfig(config);
     const { warnings, errors } = validateConfig(config);
 
     it('gets removed', () => {
-      assert.notProperty(normalizedConfig, 't');
       assert.notProperty(normalizedConfig, 'timestamp');
     });
     it('produces no warnings', () => {
@@ -339,13 +338,28 @@ describe('configuration', () => {
     });
   });
 
-  describe('with --silent/-q set', () => {
-    const config = { silent: true, q: true };
+  describe('with -t set', () => {
+    const config = { t: true };
+    const normalizedConfig = normalizeConfig(config);
+    const { warnings, errors } = validateConfig(config);
+
+    it('gets removed', () => {
+      assert.notProperty(normalizedConfig, 't');
+    });
+    it('produces no warnings', () => {
+      assert.lengthOf(warnings, 0);
+    });
+    it('produces one error', () => {
+      assert.lengthOf(errors, 1);
+    });
+  });
+
+  describe('with --silent set', () => {
+    const config = { silent: true };
     const normalizedConfig = normalizeConfig(config);
     const { warnings, errors } = validateConfig(config);
 
     it('gets removed', () => {
-      assert.notProperty(normalizedConfig, 'q');
       assert.notProperty(normalizedConfig, 'silent');
     });
     it('produces no warnings', () => {
@@ -356,13 +370,28 @@ describe('configuration', () => {
     });
   });
 
+  describe('with -q set', () => {
+    const config = { q: true };
+    const normalizedConfig = normalizeConfig(config);
+    const { warnings, errors } = validateConfig(config);
+
+    it('gets removed', () => {
+      assert.notProperty(normalizedConfig, 'q');
+    });
+    it('produces no warnings', () => {
+      assert.lengthOf(warnings, 0);
+    });
+    it('produces one error', () => {
+      assert.lengthOf(errors, 1);
+    });
+  });
+
   describe('with --sandbox/-b set', () => {
-    const config = { sandbox: true, b: true };
+    const config = { sandbox: true };
     const normalizedConfig = normalizeConfig(config);
     const { warnings, errors } = validateConfig(config);
 
     it('gets removed', () => {
-      assert.notProperty(normalizedConfig, 'b');
       assert.notProperty(normalizedConfig, 'sandbox');
     });
     it('produces no warnings', () => {
@@ -373,6 +402,22 @@ describe('configuration', () => {
     });
   });
 
+  describe('with -b set', () => {
+    const config = { b: true };
+    const normalizedConfig = normalizeConfig(config);
+    const { warnings, errors } = validateConfig(config);
+
+    it('gets removed', () => {
+      assert.notProperty(normalizedConfig, 'b');
+    });
+    it('produces no warnings', () => {
+      assert.lengthOf(warnings, 0);
+    });
+    it('produces one error', () => {
+      assert.lengthOf(errors, 1);
+    });
+  });
+
   describe('with data set to { filename: apiDescription }', () => {
     const config = { data: { 'filename.api': 'FORMAT: 1A\n# Sample API\n' } };
     const { warnings, errors } = validateConfig(config);