diff --git a/lib/assertions.js b/lib/assertions.js
index b519f19d7..9732f5a17 100644
--- a/lib/assertions.js
+++ b/lib/assertions.js
@@ -1487,7 +1487,8 @@ module.exports = expect => {
           const valueKeyType = expect.findTypeOf(valueKey);
 
           if (valueKeyType.is('expect.it')) {
-            return valueKey(subjectKey);
+            expect.context.thisObject = subject;
+            return valueKey(subjectKey, expect.context);
           } else {
             return expect(subjectKey, 'to [exhaustively] satisfy', valueKey);
           }
@@ -1498,24 +1499,28 @@ module.exports = expect => {
           expect.promise(() => {
             // create subject key presence object
             const remainingKeysInSubject = {};
-            subjectType.getKeys(subject).forEach(key => {
+            subjectKeys.forEach(key => {
               remainingKeysInSubject[key] = 1; // present in subject
             });
             // discard or mark missing each previously seen value key
             valueKeys.forEach(key => {
-              if (!remainingKeysInSubject[key]) {
+              if (
+                !remainingKeysInSubject[key] &&
+                (utils.numericalRegExp.test(key) || expect.flags.exhaustively)
+              ) {
                 remainingKeysInSubject[key] = 2; // present in value
               } else {
                 delete remainingKeysInSubject[key];
               }
             });
-            // filter outstanding keys which should not lead to an error
+            // check whether there are any outstanding keys we cannot account for
             const outstandingKeys = Object.keys(remainingKeysInSubject).filter(
               key =>
                 utils.numericalRegExp.test(key) ||
                 typeof key === 'symbol' ||
-                typeof subjectType.valueForKey(subject, key) !== 'undefined' ||
-                remainingKeysInSubject[key] === 2
+                (typeof subjectType.valueForKey(subject, key) !== 'undefined' &&
+                  // key was only in the value
+                  remainingKeysInSubject[key] === 2)
             );
             // key checking succeeds with no outstanding keys
             expect(outstandingKeys.length === 0, 'to be truthy');
diff --git a/test/assertions/to-satisfy.spec.js b/test/assertions/to-satisfy.spec.js
index 7f239ce5a..a007bb430 100644
--- a/test/assertions/to-satisfy.spec.js
+++ b/test/assertions/to-satisfy.spec.js
@@ -1451,6 +1451,65 @@ describe('to satisfy assertion', () => {
           ')'
       );
     });
+
+    it('should support context correctly with expect.it (numerical)', () => {
+      function Greeter(folks) {
+        this.push(...(folks || []));
+
+        this.greet = function(prefix) {
+          return prefix + this.join(' & ');
+        };
+      }
+
+      Greeter.prototype = [];
+
+      const clonedExpect = expect.clone();
+      clonedExpect.addType({
+        name: 'Greeter',
+        base: 'array-like',
+        identify: obj => obj instanceof Greeter
+      });
+
+      const expected = ['Alice', 'Bob'];
+      expected.greet = expect.it(
+        'when called with',
+        ['Hello, '],
+        'to equal',
+        'Hello, Alice & Bob'
+      );
+
+      clonedExpect(new Greeter(['Alice', 'Bob']), 'to satisfy', expected);
+    });
+
+    it('should support context correctly with expect.it (non-numerical)', () => {
+      function Greeter(folks) {
+        this.push(...(folks || []));
+
+        this.greet = function(prefix) {
+          return prefix + this.join(' & ');
+        };
+      }
+
+      Greeter.prototype = [];
+
+      const clonedExpect = expect.clone();
+      clonedExpect.addType({
+        name: 'Greeter',
+        base: 'array-like',
+        identify: obj => obj instanceof Greeter,
+        numericalPropertiesOnly: false
+      });
+
+      const expected = ['Alice', 'Bob'];
+      expected.greet = expect.it(
+        'when called with',
+        ['Hello, '],
+        'to equal',
+        'Hello, Alice & Bob'
+      );
+
+      clonedExpect(new Greeter(['Alice', 'Bob']), 'to satisfy', expected);
+    });
   });
 
   describe('on arrays', () => {