diff --git a/packages/bruno-app/src/components/RequestPane/Assertions/AssertionOperator/index.js b/packages/bruno-app/src/components/RequestPane/Assertions/AssertionOperator/index.js
new file mode 100644
index 00000000..993eb791
--- /dev/null
+++ b/packages/bruno-app/src/components/RequestPane/Assertions/AssertionOperator/index.js
@@ -0,0 +1,76 @@
+import React from 'react';
+
+/**
+ * Assertion operators
+ * 
+ * eq          : equal to
+ * neq         : not equal to
+ * gt          : greater than
+ * gte         : greater than or equal to
+ * lt          : less than
+ * lte         : less than or equal to
+ * in          : in
+ * notIn       : not in
+ * contains    : contains
+ * notContains : not contains
+ * length      : length
+ * matches     : matches
+ * notMatches  : not matches
+ * startsWith  : starts with
+ * endsWith    : ends with
+ * between     : between
+ * isEmpty     : is empty
+ * isNull      : is null
+ * isUndefined : is undefined
+ * isDefined   : is defined
+ * isTruthy    : is truthy
+ * isFalsy     : is falsy
+ * isJson      : is json
+ * isNumber    : is number
+ * isString    : is string
+ * isBoolean   : is boolean
+ */
+
+const AssertionOperator = ({ operator, onChange }) => {
+  const operators = [
+    'eq', 'neq', 'gt', 'gte', 'lt', 'lte', 'in', 'notIn',
+    'contains', 'notContains', 'length', 'matches', 'notMatches',
+    'startsWith', 'endsWith', 'between', 'isEmpty', 'isNull', 'isUndefined',
+    'isDefined', 'isTruthy', 'isFalsy', 'isJson', 'isNumber', 'isString', 'isBoolean'
+  ];
+
+  const handleChange = (e) => {
+    onChange(e.target.value);
+  };
+
+  const getLabel = (operator) => {
+    switch(operator) {
+      case 'eq':
+        return 'equals';
+      case 'neq':
+        return 'notEquals';
+      case 'gt':
+        return 'greaterThan';
+      case 'gte':
+        return 'greaterThanOrEqual';
+      case 'lt':
+        return 'lessThan';
+      case 'lte':
+        return 'lessThanOrEqual';
+      default:
+        return operator;
+    }
+  };
+
+  return (
+    <select value={operator} onChange={handleChange} className="mousetrap">
+      {operators.map((operator) => (
+        <option key={operator} value={operator}>
+          {getLabel(operator)}
+        </option>
+      ))}
+    </select>
+  );
+};
+
+export default AssertionOperator;
diff --git a/packages/bruno-app/src/components/RequestPane/Assertions/AssertionRow/index.js b/packages/bruno-app/src/components/RequestPane/Assertions/AssertionRow/index.js
new file mode 100644
index 00000000..bbf18ad0
--- /dev/null
+++ b/packages/bruno-app/src/components/RequestPane/Assertions/AssertionRow/index.js
@@ -0,0 +1,164 @@
+import React from 'react';
+import { IconTrash } from '@tabler/icons';
+import SingleLineEditor from 'components/SingleLineEditor';
+import AssertionOperator from '../AssertionOperator';
+import { useTheme } from 'providers/Theme';
+
+/**
+ * Assertion operators
+ * 
+ * eq          : equal to
+ * neq         : not equal to
+ * gt          : greater than
+ * gte         : greater than or equal to
+ * lt          : less than
+ * lte         : less than or equal to
+ * in          : in
+ * notIn       : not in
+ * contains    : contains
+ * notContains : not contains
+ * length      : length
+ * matches     : matches
+ * notMatches  : not matches
+ * startsWith  : starts with
+ * endsWith    : ends with
+ * between     : between
+ * isEmpty     : is empty
+ * isNull      : is null
+ * isUndefined : is undefined
+ * isDefined   : is defined
+ * isTruthy    : is truthy
+ * isFalsy     : is falsy
+ * isJson      : is json
+ * isNumber    : is number
+ * isString    : is string
+ * isBoolean   : is boolean
+ */
+const parseAssertionOperator = (str = '') => {
+  if(!str || typeof str !== 'string' || !str.length) {
+    return {
+      operator: 'eq',
+      value: str
+    };
+  }
+
+  const operators = [
+    'eq', 'neq', 'gt', 'gte', 'lt', 'lte', 'in', 'notIn',
+    'contains', 'notContains', 'length', 'matches', 'notMatches',
+    'startsWith', 'endsWith', 'between', 'isEmpty', 'isNull', 'isUndefined',
+    'isDefined', 'isTruthy', 'isFalsy', 'isJson', 'isNumber', 'isString', 'isBoolean'
+  ];
+
+  const unaryOperators = [
+    'isEmpty', 'isNull', 'isUndefined', 'isDefined', 'isTruthy', 'isFalsy', 'isJson', 'isNumber', 'isString', 'isBoolean'
+  ];
+
+  const [operator, ...rest] = str.trim().split(' ');
+  const value = rest.join(' ');
+
+  if(unaryOperators.includes(operator)) {
+    return {
+      operator,
+      value: ''
+    };
+  }
+
+  if(operators.includes(operator)) {
+    return {
+      operator,
+      value
+    };
+  }
+
+  return {
+    operator: 'eq',
+    value: str
+  };
+};
+
+const isUnaryOperator = (operator) => {
+  const unaryOperators = [
+    'isEmpty', 'isNull', 'isUndefined', 'isDefined', 'isTruthy', 'isFalsy', 'isJson', 'isNumber', 'isString', 'isBoolean'
+  ];
+
+  return unaryOperators.includes(operator);
+};
+
+const AssertionRow = ({
+  item, collection, assertion, handleAssertionChange, handleRemoveAssertion,
+  onSave, handleRun
+}) => {
+  const { storedTheme } = useTheme();
+
+  const {
+    operator,
+    value
+  } = parseAssertionOperator(assertion.value);
+  console.log(operator);
+  console.log(value);
+
+  return (
+    <tr key={assertion.uid}>
+      <td>
+        <input
+          type="text"
+          autoComplete="off"
+          autoCorrect="off"
+          autoCapitalize="off"
+          spellCheck="false"
+          value={assertion.name}
+          className="mousetrap"
+          onChange={(e) => handleAssertionChange(e, assertion, 'name')}
+        />
+      </td>
+      <td>
+        <AssertionOperator
+          operator={operator}
+          onChange={(op) => handleAssertionChange({
+            target: {
+              value: `${op} ${value}`
+            }
+          }, assertion, 'value')}
+        />
+      </td>
+      <td>
+        {!isUnaryOperator(operator) ? (
+          <SingleLineEditor
+            value={value}
+            theme={storedTheme}
+            readOnly={true}
+            onSave={onSave}
+            onChange={(newValue) => handleAssertionChange({
+              target: {
+                value: newValue
+              }
+            }, assertion, 'value')}
+            onRun={handleRun}
+            collection={collection}
+          />
+        ) : (
+          <input
+            type="text"
+            className='cursor-default'
+            disabled
+          />
+        )}
+      </td>
+      <td>
+        <div className="flex items-center">
+          <input
+            type="checkbox"
+            checked={assertion.enabled}
+            className="mr-3 mousetrap"
+            onChange={(e) => handleAssertionChange(e, assertion, 'enabled')}
+          />
+          <button onClick={() => handleRemoveAssertion(assertion)}>
+            <IconTrash strokeWidth={1.5} size={20} />
+          </button>
+        </div>
+      </td>
+    </tr>
+  );
+};
+
+export default AssertionRow;
diff --git a/packages/bruno-app/src/components/RequestPane/Assert/StyledWrapper.js b/packages/bruno-app/src/components/RequestPane/Assertions/StyledWrapper.js
similarity index 97%
rename from packages/bruno-app/src/components/RequestPane/Assert/StyledWrapper.js
rename to packages/bruno-app/src/components/RequestPane/Assertions/StyledWrapper.js
index b7c95b47..7357a74b 100644
--- a/packages/bruno-app/src/components/RequestPane/Assert/StyledWrapper.js
+++ b/packages/bruno-app/src/components/RequestPane/Assertions/StyledWrapper.js
@@ -24,7 +24,7 @@ const Wrapper = styled.div`
         width: 30%;
       }
 
-      &:nth-child(3) {
+      &:nth-child(4) {
         width: 70px;
       }
     }
diff --git a/packages/bruno-app/src/components/RequestPane/Assert/index.js b/packages/bruno-app/src/components/RequestPane/Assertions/index.js
similarity index 52%
rename from packages/bruno-app/src/components/RequestPane/Assert/index.js
rename to packages/bruno-app/src/components/RequestPane/Assertions/index.js
index 256a77c9..1805a632 100644
--- a/packages/bruno-app/src/components/RequestPane/Assert/index.js
+++ b/packages/bruno-app/src/components/RequestPane/Assertions/index.js
@@ -1,17 +1,14 @@
 import React from 'react';
 import get from 'lodash/get';
 import cloneDeep from 'lodash/cloneDeep';
-import { IconTrash } from '@tabler/icons';
 import { useDispatch } from 'react-redux';
-import { useTheme } from 'providers/Theme';
 import { addAssertion, updateAssertion, deleteAssertion } from 'providers/ReduxStore/slices/collections';
 import { sendRequest, saveRequest } from 'providers/ReduxStore/slices/collections/actions';
-import SingleLineEditor from 'components/SingleLineEditor';
+import AssertionRow from './AssertionRow';
 import StyledWrapper from './StyledWrapper';
 
 const Assertions = ({ item, collection }) => {
   const dispatch = useDispatch();
-  const { storedTheme } = useTheme();
   const assertions = item.draft ? get(item, 'draft.request.assertions') : get(item, 'request.assertions');
 
   const handleAddAssertion = () => {
@@ -66,55 +63,25 @@ const Assertions = ({ item, collection }) => {
         <thead>
           <tr>
             <td>Expr</td>
+            <td>Operator</td>
             <td>Value</td>
             <td></td>
           </tr>
         </thead>
         <tbody>
           {assertions && assertions.length
-            ? assertions.map((assertion, index) => {
+            ? assertions.map((assertion) => {
                 return (
-                  <tr key={assertion.uid}>
-                    <td>
-                      <input
-                        type="text"
-                        autoComplete="off"
-                        autoCorrect="off"
-                        autoCapitalize="off"
-                        spellCheck="false"
-                        value={assertion.name}
-                        className="mousetrap"
-                        onChange={(e) => handleAssertionChange(e, assertion, 'name')}
-                      />
-                    </td>
-                    <td>
-                      <SingleLineEditor
-                        value={assertion.value}
-                        theme={storedTheme}
-                        onSave={onSave}
-                        onChange={(newValue) => handleAssertionChange({
-                          target: {
-                            value: newValue
-                          }
-                        }, assertion, 'value')}
-                        onRun={handleRun}
-                        collection={collection}
-                      />
-                    </td>
-                    <td>
-                      <div className="flex items-center">
-                        <input
-                          type="checkbox"
-                          checked={assertion.enabled}
-                          className="mr-3 mousetrap"
-                          onChange={(e) => handleAssertionChange(e, assertion, 'enabled')}
-                        />
-                        <button onClick={() => handleRemoveAssertion(assertion)}>
-                          <IconTrash strokeWidth={1.5} size={20} />
-                        </button>
-                      </div>
-                    </td>
-                  </tr>
+                  <AssertionRow
+                    key={assertion.uid}
+                    assertion={assertion}
+                    item={item}
+                    collection={collection}
+                    handleAssertionChange={handleAssertionChange}
+                    handleRemoveAssertion={handleRemoveAssertion}
+                    onSave={onSave}
+                    handleRun={handleRun}
+                  />
                 );
               })
             : null}
diff --git a/packages/bruno-app/src/components/RequestPane/HttpRequestPane/index.js b/packages/bruno-app/src/components/RequestPane/HttpRequestPane/index.js
index 5ddf2393..55da6c9c 100644
--- a/packages/bruno-app/src/components/RequestPane/HttpRequestPane/index.js
+++ b/packages/bruno-app/src/components/RequestPane/HttpRequestPane/index.js
@@ -8,7 +8,7 @@ import RequestHeaders from 'components/RequestPane/RequestHeaders';
 import RequestBody from 'components/RequestPane/RequestBody';
 import RequestBodyMode from 'components/RequestPane/RequestBody/RequestBodyMode';
 import Vars from 'components/RequestPane/Vars';
-import Assert from 'components/RequestPane/Assert';
+import Assertions from 'components/RequestPane/Assertions';
 import Script from 'components/RequestPane/Script';
 import Tests from 'components/RequestPane/Tests';
 import StyledWrapper from './StyledWrapper';
@@ -42,7 +42,7 @@ const HttpRequestPane = ({ item, collection, leftPaneWidth }) => {
         return <Vars item={item} collection={collection} />;
       }
       case 'assert': {
-        return <Assert item={item} collection={collection} />;
+        return <Assertions item={item} collection={collection} />;
       }
       case 'script': {
         return <Script item={item} collection={collection} />;
diff --git a/packages/bruno-js/src/runtime/assert-runtime.js b/packages/bruno-js/src/runtime/assert-runtime.js
index 44e916cf..89ccddfb 100644
--- a/packages/bruno-js/src/runtime/assert-runtime.js
+++ b/packages/bruno-js/src/runtime/assert-runtime.js
@@ -11,7 +11,6 @@ const { expect } = chai;
  * 
  * eq          : equal to
  * neq         : not equal to
- * like        : like
  * gt          : greater than
  * gte         : greater than or equal to
  * lt          : less than
@@ -20,7 +19,6 @@ const { expect } = chai;
  * notIn       : not in
  * contains    : contains
  * notContains : not contains
- * count       : count
  * length      : length
  * matches     : matches
  * notMatches  : not matches
@@ -47,8 +45,8 @@ const parseAssertionOperator = (str = '') => {
   }
 
   const operators = [
-    'eq', 'neq', 'like', 'gt', 'gte', 'lt', 'lte', 'in', 'notIn',
-    'contains', 'notContains', 'count', 'length', 'matches', 'notMatches',
+    'eq', 'neq', 'gt', 'gte', 'lt', 'lte', 'in', 'notIn',
+    'contains', 'notContains', 'length', 'matches', 'notMatches',
     'startsWith', 'endsWith', 'between', 'isEmpty', 'isNull', 'isUndefined',
     'isDefined', 'isTruthy', 'isFalsy', 'isJson', 'isNumber', 'isString', 'isBoolean'
   ];
@@ -114,9 +112,6 @@ class AssertRuntime {
           case 'neq':
             expect(lhs).to.not.equal(rhs);
             break;
-          case 'like':
-            expect(lhs).to.match(new RegExp(rhs));
-            break;
           case 'gt':
             expect(lhs).to.be.greaterThan(rhs);
             break;
@@ -141,9 +136,6 @@ class AssertRuntime {
           case 'notContains':
             expect(lhs).to.not.include(rhs);
             break;
-          case 'count':
-            expect(lhs).to.have.lengthOf(rhs);
-            break;
           case 'length':
             expect(lhs).to.have.lengthOf(rhs);
             break;
@@ -160,7 +152,7 @@ class AssertRuntime {
             expect(lhs).to.endWith(rhs);
             break;
           case 'between':
-            const [min, max] = value.split(' ');
+            const [min, max] = value.split(',');
             expect(lhs).to.be.within(min, max);
             break;
           case 'isEmpty':