diff --git a/config/endpoint/endpoint.go b/config/endpoint/endpoint.go
index e73d4075..bfc57872 100644
--- a/config/endpoint/endpoint.go
+++ b/config/endpoint/endpoint.go
@@ -123,7 +123,7 @@ type Endpoint struct {
 	NumberOfSuccessesInARow int `yaml:"-"`
 
 	// LastReminderSent is the time at which the last reminder was sent for this endpoint.
-	LastReminderSent time.Time `yaml:"-"`
+	LastReminderSent map[alert.Type]time.Time `yaml:"-"`
 }
 
 // IsEnabled returns whether the endpoint is enabled or not
@@ -193,6 +193,9 @@ func (e *Endpoint) ValidateAndSetDefaults() error {
 	if len(e.Headers) == 0 {
 		e.Headers = make(map[string]string)
 	}
+	if len(e.LastReminderSent) == 0 {
+		e.LastReminderSent = make(map[alert.Type]time.Time)
+	}
 	// Automatically add user agent header if there isn't one specified in the endpoint configuration
 	if _, userAgentHeaderExists := e.Headers[UserAgentHeader]; !userAgentHeaderExists {
 		e.Headers[UserAgentHeader] = GatusUserAgent
diff --git a/config/endpoint/external_endpoint.go b/config/endpoint/external_endpoint.go
index 58f37fed..8527187c 100644
--- a/config/endpoint/external_endpoint.go
+++ b/config/endpoint/external_endpoint.go
@@ -2,6 +2,7 @@ package endpoint
 
 import (
 	"errors"
+	"time"
 
 	"github.com/TwiN/gatus/v5/alerting/alert"
 )
@@ -75,6 +76,8 @@ func (externalEndpoint *ExternalEndpoint) ToEndpoint() *Endpoint {
 		Enabled:                 externalEndpoint.Enabled,
 		Name:                    externalEndpoint.Name,
 		Group:                   externalEndpoint.Group,
+		Headers:                 make(map[string]string),
+		LastReminderSent:        make(map[alert.Type]time.Time),
 		Alerts:                  externalEndpoint.Alerts,
 		NumberOfFailuresInARow:  externalEndpoint.NumberOfFailuresInARow,
 		NumberOfSuccessesInARow: externalEndpoint.NumberOfSuccessesInARow,
diff --git a/watchdog/alerting.go b/watchdog/alerting.go
index 72cacb19..99d2ee03 100644
--- a/watchdog/alerting.go
+++ b/watchdog/alerting.go
@@ -35,16 +35,16 @@ func handleAlertsToTrigger(ep *endpoint.Endpoint, result *endpoint.Result, alert
 		sendInitialAlert := !endpointAlert.Triggered
 		// Determine if a reminder should be sent
 		var lastReminder time.Duration
-		if !ep.LastReminderSent.IsZero() {
-			lastReminder = time.Since(ep.LastReminderSent)
+		if lr, ok := ep.LastReminderSent[endpointAlert.Type]; ok && !lr.IsZero() {
+			lastReminder = time.Since(lr)
 		}
 		sendReminder := endpointAlert.Triggered && endpointAlert.RepeatInterval > 0 &&
 			(lastReminder == 0 || lastReminder >= endpointAlert.RepeatInterval)
 		// If neither initial alert nor reminder needs to be sent, skip to the next alert
 		if !sendInitialAlert && !sendReminder {
 			if debug {
-				log.Printf("[watchdog.handleAlertsToTrigger] Alert for endpoint=%s with description='%s' is not due for triggering or reminding (interval: %s last: %s), skipping",
-					ep.Name, endpointAlert.GetDescription(), endpointAlert.RepeatInterval, lastReminder)
+				log.Printf("[watchdog.handleAlertsToTrigger] Alert %s for endpoint=%s with description='%s' is not due for triggering (interval: %s last: %s), skipping",
+					endpointAlert.Type, ep.Name, endpointAlert.GetDescription(), endpointAlert.RepeatInterval, lastReminder)
 			}
 			continue
 		}
@@ -70,7 +70,7 @@ func handleAlertsToTrigger(ep *endpoint.Endpoint, result *endpoint.Result, alert
 				if sendInitialAlert {
 					endpointAlert.Triggered = true
 				}
-				ep.LastReminderSent = time.Now()
+				ep.LastReminderSent[endpointAlert.Type] = time.Now()
 				if err := store.Get().UpsertTriggeredEndpointAlert(ep, endpointAlert); err != nil {
 					log.Printf("[watchdog.handleAlertsToTrigger] Failed to persist triggered endpoint alert for endpoint with key=%s: %s", ep.Key(), err.Error())
 				}
@@ -113,7 +113,7 @@ func handleAlertsToResolve(ep *endpoint.Endpoint, result *endpoint.Result, alert
 		} else {
 			log.Printf("[watchdog.handleAlertsToResolve] Not sending alert of type=%s despite being RESOLVED, because the provider wasn't configured properly", endpointAlert.Type)
 		}
+		ep.LastReminderSent[endpointAlert.Type] = time.Now()
 	}
 	ep.NumberOfFailuresInARow = 0
-	ep.LastReminderSent = time.Now()
 }