diff --git a/lib/document.js b/lib/document.js
index afc9e5ceac..1f0e9d332a 100644
--- a/lib/document.js
+++ b/lib/document.js
@@ -2770,15 +2770,6 @@ function _getPathsToValidate(doc, pathsToValidate, pathsToSkip) {
     }
   }
 
-  for (const path of paths) {
-    // Single nested paths (paths embedded under single nested subdocs) will
-    // be validated on their own when we call `validate()` on the subdoc itself.
-    // Re: gh-8468
-    if (doc.$__schema.singleNestedPaths.hasOwnProperty(path)) {
-      paths.delete(path);
-      continue;
-    }
-  }
 
   if (Array.isArray(pathsToValidate)) {
     paths = _handlePathsToValidate(paths, pathsToValidate);
@@ -2800,7 +2791,10 @@ function _getPathsToValidate(doc, pathsToValidate, pathsToSkip) {
         _v = _v.toObject({ transform: false });
       }
       const flat = flatten(_v, pathToCheck, flattenOptions, doc.$__schema);
-      Object.keys(flat).forEach(addToPaths);
+      // Single nested paths (paths embedded under single nested subdocs) will
+      // be validated on their own when we call `validate()` on the subdoc itself.
+      // Re: gh-8468
+      Object.keys(flat).filter(path => !doc.$__schema.singleNestedPaths.hasOwnProperty(path)).forEach(addToPaths);
     }
   }
 
diff --git a/test/document.test.js b/test/document.test.js
index f65479224d..f1563c3006 100644
--- a/test/document.test.js
+++ b/test/document.test.js
@@ -13782,6 +13782,64 @@ describe('document', function() {
     assert.strictEqual(doc.toObject().labPlots[0].lab.capacityLevelCeil, 4);
     assert.strictEqual(doc.toJSON().labPlots[0].lab.capacityLevelCeil, 4);
   });
+
+  it('calls required with correct context on single nested properties (gh-14788)', async function() {
+    const requiredCalls = [];
+    function createCustomSchema() {
+      return new mongoose.Schema({
+        prop1: {
+          type: String,
+          required() {
+            requiredCalls.push(this);
+            return this.prop1 === undefined;
+          },
+          validate: {
+            validator(prop1) {
+              if (this.prop2 !== null && prop1 != null) {
+                throw new Error('cannot use prop1 if prop2 is defined!');
+              }
+              return true;
+            }
+          }
+        },
+        prop2: {
+          type: String,
+          required() {
+            requiredCalls.push(this);
+            return this.prop2 === undefined;
+          },
+          validate: {
+            validator(prop2) {
+              if (this.prop1 === null && prop2 === null) {
+                throw new Error('cannot be null if prop1 is missing!');
+              }
+              return true;
+            }
+          }
+        }
+      }, { _id: false });
+    }
+
+    const schema = new mongoose.Schema({
+      config: {
+        prop: {
+          type: createCustomSchema(),
+          required: true
+        }
+      }
+    });
+
+    const TestModel = db.model('Test', schema);
+    const doc = new TestModel({
+      config: {
+        prop: { prop1: null, prop2: 'test-value' }
+      }
+    });
+    await doc.validate();
+    assert.equal(requiredCalls.length, 2);
+    assert.strictEqual(requiredCalls[0], doc.config.prop);
+    assert.strictEqual(requiredCalls[1], doc.config.prop);
+  });
 });
 
 describe('Check if instance function that is supplied in schema option is available', function() {