diff --git a/main.go b/main.go
index 9a5c3ed..68bddd6 100644
--- a/main.go
+++ b/main.go
@@ -420,15 +420,24 @@ func calculateShift(transactionLog TransactionLog, transaction Transaction) time
 	return transactionLog.nextLogDay(transaction.Date).Date
 }
 
-func (tl *TransactionLog) delayTransaction(transaction *Transaction) {
+func (tl *TransactionLog) delayTransaction(transaction *Transaction) bool {
 	newDate := calculateShift(*tl, *transaction)
 
+	if newDate.Before(currentDay()) {
+		logrus.Debugf("Transaction presumed executed in the past %s (%s | %f)",
+			transaction.ID, transaction.Name, transaction.Amount)
+		delete(tl.LogDays[transaction.Date].Transactions, transaction.ID)
+		return false
+	}
+
 	if newDate.Before(tl.first()) || newDate == transaction.Date {
 		logrus.Debugf("Transaction not delayable %s (%s | %f)", transaction.ID, transaction.Name, transaction.Amount)
 		transaction.Delayable = false
-		return
+		return false
 	}
 
+	delete(tl.LogDays[transaction.Date].Transactions, transaction.ID)
+
 	if newDate.After(tl.last()) {
 		newDate = tl.last()
 	}
@@ -439,8 +448,6 @@ func (tl *TransactionLog) delayTransaction(transaction *Transaction) {
 
 	tl.addDay(newDate)
 
-	delete(tl.LogDays[transaction.Date].Transactions, transaction.ID)
-
 	transaction.Date = newDate
 	tl.LogDays[newDate].Transactions[transaction.ID] = transaction
 
@@ -449,6 +456,7 @@ func (tl *TransactionLog) delayTransaction(transaction *Transaction) {
 		transaction.DelayedReason = DelayInsufficient
 	}
 
+	return true
 }
 
 func (tl *TransactionLog) executeTransaction(transaction *Transaction) bool {
@@ -457,9 +465,11 @@ func (tl *TransactionLog) executeTransaction(transaction *Transaction) bool {
 	copy(accounts, logDay.EndingBalance)
 
 	if isWeekend(transaction.Date) && transaction.Delayable {
-		logrus.Debugf("Delaying %s due to weekend scheduling\n", transaction.Name)
-		tl.delayTransaction(transaction)
-		transaction.DelayedReason = DelayWeekend
+		delayed := tl.delayTransaction(transaction)
+		if delayed {
+			logrus.Debugf("Delaying %s to %s due to weekend scheduling\n", transaction.Name, transaction.Date.String())
+			transaction.DelayedReason = DelayWeekend
+		}
 
 		return false
 	}
@@ -467,9 +477,9 @@ func (tl *TransactionLog) executeTransaction(transaction *Transaction) bool {
 	logrus.Debugf("Balance: %f | Minimum: %f\n", accounts[0].Balance, accounts[0].Minimum)
 	logrus.Debugf("Delayable: %t", transaction.Delayable)
 	if !isAffordable(transaction.Amount, accounts[0].Balance, accounts[0].Minimum) && transaction.Delayable {
-		logrus.Debugf("Delaying %s: %f (%s) due to lack of funds\n",
-			transaction.Name, transaction.Amount, transaction.Date)
 		tl.delayTransaction(transaction)
+		logrus.Debugf("Delaying %s to %s: %f (%s) due to lack of funds\n",
+			transaction.Name, transaction.Date.String(), transaction.Amount, transaction.Date)
 
 		return false
 	}