diff --git a/packages/core/database/lib/query/helpers/where.js b/packages/core/database/lib/query/helpers/where.js
index a899bb55a6..f164b8560e 100644
--- a/packages/core/database/lib/query/helpers/where.js
+++ b/packages/core/database/lib/query/helpers/where.js
@@ -60,13 +60,17 @@ const castValue = (value, attribute) => {
   return value;
 };
 
-const processAttributeWhere = (attribute, where, ctx) => {
+const processAttributeWhere = (attribute, where, operator = '$eq') => {
   if (_.isArray(where)) {
-    return where.map(sub => processAttributeWhere(attribute, sub, ctx));
+    return where.map(sub => processAttributeWhere(attribute, sub, operator));
   }
 
   if (!_.isPlainObject(where)) {
-    return castValue(where, attribute);
+    if (CAST_OPERATORS.includes(operator)) {
+      return castValue(where, attribute);
+    }
+
+    return where;
   }
 
   const filters = {};
@@ -74,21 +78,11 @@ const processAttributeWhere = (attribute, where, ctx) => {
   for (const key in where) {
     const value = where[key];
 
-    if (isOperator(key)) {
-      if (!_.isPlainObject(value)) {
-        if (CAST_OPERATORS.includes(key)) {
-          filters[key] = castValue(value, attribute);
-        } else {
-          filters[key] = value;
-        }
-        continue;
-      }
-
-      filters[key] = processAttributeWhere(attribute, value, ctx);
-      continue;
+    if (!isOperator(key)) {
+      throw new Error(`Undefined attribute level operator ${key}`);
     }
 
-    throw new Error(`Undefined attribute level operator ${key}`);
+    filters[key] = processAttributeWhere(attribute, value, key);
   }
 
   return filters;
@@ -145,7 +139,7 @@ const processWhere = (where, ctx) => {
     const attribute = meta.attributes[key];
 
     if (!attribute) {
-      filters[qb.aliasColumn(key, alias)] = processAttributeWhere(null, value, ctx);
+      filters[qb.aliasColumn(key, alias)] = processAttributeWhere(null, value);
       continue;
     }
 
@@ -179,7 +173,7 @@ const processWhere = (where, ctx) => {
       const columnName = toColumnName(meta, key);
       const aliasedColumnName = qb.aliasColumn(columnName, alias);
 
-      filters[aliasedColumnName] = processAttributeWhere(attribute, value, ctx);
+      filters[aliasedColumnName] = processAttributeWhere(attribute, value);
 
       continue;
     }
diff --git a/packages/core/strapi/tests/filtering.test.e2e.js b/packages/core/strapi/tests/filtering.test.e2e.js
index b8384457b2..7b06d8ee92 100644
--- a/packages/core/strapi/tests/filtering.test.e2e.js
+++ b/packages/core/strapi/tests/filtering.test.e2e.js
@@ -35,6 +35,9 @@ const product = {
     big_rank: {
       type: 'biginteger',
     },
+    isChecked: {
+      type: 'boolean',
+    },
   },
   displayName: 'Product',
   singularName: 'product',
@@ -51,6 +54,7 @@ const productFixtures = [
     decimal_field: 42.43,
     rank: 42,
     big_rank: '345678912983',
+    isChecked: true,
   },
   {
     name: 'Product 2',
@@ -59,6 +63,7 @@ const productFixtures = [
     decimal_field: 91.22,
     rank: 82,
     big_rank: '926371623421',
+    isChecked: false,
   },
   {
     name: 'Product 3',
@@ -67,6 +72,7 @@ const productFixtures = [
     decimal_field: 12.22,
     rank: 91,
     big_rank: '926372323421',
+    isChecked: true,
   },
   {
     name: 'Product 4',
@@ -75,6 +81,7 @@ const productFixtures = [
     decimal_field: 12.22,
     rank: 99,
     big_rank: '999999999999',
+    isChecked: false,
   },
   {
     name: 'Продукт 5, Product 5',
@@ -83,6 +90,7 @@ const productFixtures = [
     decimal_field: 142.43,
     rank: 142,
     big_rank: 345678912983,
+    isChecked: true,
   },
 ];
 
@@ -1376,4 +1384,100 @@ describe('Filtering API', () => {
       expect(res.body.data).toEqual(expect.arrayContaining([data.product[4]]));
     });
   });
+
+  describe('Type casting', () => {
+    describe('Booleans', () => {
+      test.each(['1', 'true', true, 't'])('Cast truthy booleans %s', async val => {
+        const res = await rq({
+          method: 'GET',
+          url: '/products',
+          qs: {
+            filters: {
+              isChecked: val,
+            },
+          },
+        });
+        expect(res.body.data).toEqual(
+          expect.arrayContaining([data.product[0], data.product[2], data.product[4]])
+        );
+      });
+
+      test.each(['1', 'true', true, 't'])('Cast truthy booleans nested %s', async val => {
+        const res = await rq({
+          method: 'GET',
+          url: '/products',
+          qs: {
+            filters: {
+              isChecked: {
+                $eq: val,
+              },
+            },
+          },
+        });
+        expect(res.body.data).toEqual(
+          expect.arrayContaining([data.product[0], data.product[2], data.product[4]])
+        );
+      });
+
+      test.each(['1', 'true', true, 't'])('Cast truthy booleans in arrays %s', async val => {
+        const res = await rq({
+          method: 'GET',
+          url: '/products',
+          qs: {
+            filters: {
+              isChecked: {
+                $in: [val],
+              },
+            },
+          },
+        });
+        expect(res.body.data).toEqual(
+          expect.arrayContaining([data.product[0], data.product[2], data.product[4]])
+        );
+      });
+
+      test.each(['0', 'false', false, 'f'])('Cast truthy booleans %s', async val => {
+        const res = await rq({
+          method: 'GET',
+          url: '/products',
+          qs: {
+            filters: {
+              isChecked: val,
+            },
+          },
+        });
+        expect(res.body.data).toEqual(expect.arrayContaining([data.product[1], data.product[3]]));
+      });
+
+      test.each(['0', 'false', false, 'f'])('Cast truthy booleans nested %s', async val => {
+        const res = await rq({
+          method: 'GET',
+          url: '/products',
+          qs: {
+            filters: {
+              isChecked: {
+                $eq: val,
+              },
+            },
+          },
+        });
+        expect(res.body.data).toEqual(expect.arrayContaining([data.product[1], data.product[3]]));
+      });
+
+      test.each(['0', 'false', false, 'f'])('Cast truthy booleans in arrays %s', async val => {
+        const res = await rq({
+          method: 'GET',
+          url: '/products',
+          qs: {
+            filters: {
+              isChecked: {
+                $in: [val],
+              },
+            },
+          },
+        });
+        expect(res.body.data).toEqual(expect.arrayContaining([data.product[1], data.product[3]]));
+      });
+    });
+  });
 });