diff --git a/packages/loot-core/src/server/transactions/transaction-rules.test.ts b/packages/loot-core/src/server/transactions/transaction-rules.test.ts
index 4fda79077d..ff8d5bbdbe 100644
--- a/packages/loot-core/src/server/transactions/transaction-rules.test.ts
+++ b/packages/loot-core/src/server/transactions/transaction-rules.test.ts
@@ -406,6 +406,74 @@ describe('Transaction rules', () => {
     });
   });
 
+  test('"payee is nothing" matches a transaction without a payee field', async () => {
+    await loadRules();
+    await insertRule({
+      stage: null,
+      conditionsOp: 'and',
+      conditions: [{ op: 'is', field: 'payee', value: null }],
+      actions: [{ op: 'set', field: 'notes', value: 'no payee' }],
+    });
+
+    // Bank sync leaves `payee` out entirely when the import has no payee
+    expect(
+      await runRules({
+        imported_payee: 'kroger',
+        date: '2020-08-11',
+        amount: 50,
+      }),
+    ).toEqual({
+      imported_payee: 'kroger',
+      date: '2020-08-11',
+      amount: 50,
+      notes: 'no payee',
+    });
+
+    // A payee set by a rule action is kept
+    await insertRule({
+      stage: null,
+      conditionsOp: 'and',
+      conditions: [{ op: 'is', field: 'payee', value: null }],
+      actions: [{ op: 'set', field: 'payee', value: 'kroger' }],
+    });
+    expect(
+      await runRules({
+        imported_payee: 'kroger',
+        date: '2020-08-11',
+        amount: 50,
+      }),
+    ).toEqual({
+      imported_payee: 'kroger',
+      date: '2020-08-11',
+      amount: 50,
+      payee: 'kroger',
+      notes: 'no payee',
+    });
+  });
+
+  test('"category is nothing" matches a transaction without a category field', async () => {
+    await loadRules();
+    await insertRule({
+      stage: null,
+      conditionsOp: 'and',
+      conditions: [{ op: 'is', field: 'category', value: null }],
+      actions: [{ op: 'set', field: 'notes', value: 'no category' }],
+    });
+
+    expect(
+      await runRules({
+        payee: 'kroger',
+        date: '2020-08-11',
+        amount: 50,
+      }),
+    ).toEqual({
+      payee: 'kroger',
+      date: '2020-08-11',
+      amount: 50,
+      notes: 'no category',
+    });
+  });
+
   test('category_group condition matches categories in that group (live)', async () => {
     await loadRules();
     const billsGroupId = await db.insertCategoryGroup({ name: 'Bills' });
diff --git a/packages/loot-core/src/server/transactions/transaction-rules.ts b/packages/loot-core/src/server/transactions/transaction-rules.ts
index a3e3329ad3..26af124d99 100644
--- a/packages/loot-core/src/server/transactions/transaction-rules.ts
+++ b/packages/loot-core/src/server/transactions/transaction-rules.ts
@@ -318,6 +318,8 @@ export async function getAllRuleIdsFromSchedules(
 }
 
 // Runner
+const NULLABLE_RULE_FIELDS = ['payee', 'category'] as const;
+
 export async function runRules(
   trans,
   accounts: Map<string, db.DbAccount> | null = null,
@@ -340,9 +342,24 @@ export async function runRules(
     ),
   );
 
-  let finalTrans = await prepareTransactionForRules({ ...trans }, accountsMap, {
-    includeBalance: false,
-  });
+  // Bank sync and the client can leave `payee` or `category` out entirely
+  // when the transaction has none. A condition never matches a missing
+  // field, so a "payee is nothing" rule would silently skip such a
+  // transaction. Match against null instead, and drop the field again
+  // afterwards so the returned shape matches the input.
+  const missingNullableFields = NULLABLE_RULE_FIELDS.filter(
+    field => trans[field] === undefined,
+  );
+  const normalizedTrans = { ...trans };
+  for (const field of missingNullableFields) {
+    normalizedTrans[field] = null;
+  }
+
+  let finalTrans = await prepareTransactionForRules(
+    normalizedTrans,
+    accountsMap,
+    { includeBalance: false },
+  );
   let lastCategoryIdForGroup: string | null = finalTrans.category ?? null;
 
   // The running balance is a query over every earlier transaction in
@@ -431,7 +448,13 @@ export async function runRules(
     }
   }
 
-  return await finalizeTransactionForRules(finalTrans);
+  const result = await finalizeTransactionForRules(finalTrans);
+  for (const field of missingNullableFields) {
+    if (result[field] === null) {
+      delete result[field];
+    }
+  }
+  return result;
 }
 
 function conditionSpecialCases(cond: Condition | null): Condition | null {
diff --git a/upcoming-release-notes/rules-payee-is-nothing.md b/upcoming-release-notes/rules-payee-is-nothing.md
new file mode 100644
index 0000000000..33c4a03530
--- /dev/null
+++ b/upcoming-release-notes/rules-payee-is-nothing.md
@@ -0,0 +1,6 @@
+---
+category: Bugfix
+authors: [YasinzHyper]
+---
+
+Fix "payee is nothing" and "category is nothing" rule conditions not matching synced transactions that have no payee or category