diff --git a/README.md b/README.md
index 722c9677..892364f5 100644
--- a/README.md
+++ b/README.md
@@ -95,10 +95,10 @@ Note that you can also add environment variables in the configuration file (i.e.
 | `services`                               | List of services to monitor                                                   | Required `[]`  |
 | `services[].name`                        | Name of the service. Can be anything.                                         | Required `""`  |
 | `services[].url`                         | URL to send the request to                                                    | Required `""`  |
-| `services[].conditions`                  | Conditions used to determine the health of the service                        | `[]`           |
-| `services[].insecure`                    | Whether to skip verifying the server's certificate chain and host name        | `false`        |
-| `services[].interval`                    | Duration to wait between every status check                                   | `60s`          |
 | `services[].method`                      | Request method                                                                | `GET`          |
+| `services[].insecure`                    | Whether to skip verifying the server's certificate chain and host name        | `false`        |
+| `services[].conditions`                  | Conditions used to determine the health of the service                        | `[]`           |
+| `services[].interval`                    | Duration to wait between every status check                                   | `60s`          |
 | `services[].graphql`                     | Whether to wrap the body in a query param (`{"query":"$body"}`)               | `false`        |
 | `services[].body`                        | Request body                                                                  | `""`           |
 | `services[].headers`                     | Request headers                                                               | `{}`           |
@@ -120,6 +120,8 @@ Note that you can also add environment variables in the configuration file (i.e.
 | `alerting.twilio.to`                     | Number to send twilio alerts to                                               | Required `""`  |
 | `alerting.custom`                        | Configuration for custom actions on failure or alerts                         | `{}`           |
 | `alerting.custom.url`                    | Custom alerting request url                                                   | Required `""`  |
+| `alerting.custom.method`                 | Request method                                                                | `GET`          |
+| `alerting.custom.insecure`               | Whether to skip verifying the server's certificate chain and host name        | `false`        |
 | `alerting.custom.body`                   | Custom alerting request body.                                                 | `""`           |
 | `alerting.custom.headers`                | Custom alerting request headers                                               | `{}`           |
 | `security`                               | Security configuration                                                        | `{}`           |
diff --git a/alerting/provider/custom/custom.go b/alerting/provider/custom/custom.go
index e0b5cad9..a2980b31 100644
--- a/alerting/provider/custom/custom.go
+++ b/alerting/provider/custom/custom.go
@@ -3,20 +3,22 @@ package custom
 import (
 	"bytes"
 	"fmt"
-	"github.com/TwinProduction/gatus/client"
-	"github.com/TwinProduction/gatus/core"
 	"io/ioutil"
 	"net/http"
 	"strings"
+
+	"github.com/TwinProduction/gatus/client"
+	"github.com/TwinProduction/gatus/core"
 )
 
 // AlertProvider is the configuration necessary for sending an alert using a custom HTTP request
 // Technically, all alert providers should be reachable using the custom alert provider
 type AlertProvider struct {
-	URL     string            `yaml:"url"`
-	Method  string            `yaml:"method,omitempty"`
-	Body    string            `yaml:"body,omitempty"`
-	Headers map[string]string `yaml:"headers,omitempty"`
+	URL      string            `yaml:"url"`
+	Method   string            `yaml:"method,omitempty"`
+	Insecure bool              `yaml:"insecure,omitempty"`
+	Body     string            `yaml:"body,omitempty"`
+	Headers  map[string]string `yaml:"headers,omitempty"`
 }
 
 // IsValid returns whether the provider's configuration is valid
@@ -73,7 +75,7 @@ func (provider *AlertProvider) buildRequest(serviceName, alertDescription string
 // Send a request to the alert provider and return the body
 func (provider *AlertProvider) Send(serviceName, alertDescription string, resolved bool) ([]byte, error) {
 	request := provider.buildRequest(serviceName, alertDescription, resolved)
-	response, err := client.GetHTTPClient(false).Do(request)
+	response, err := client.GetHTTPClient(provider.Insecure).Do(request)
 	if err != nil {
 		return nil, err
 	}
diff --git a/config/config_test.go b/config/config_test.go
index 8e97c87d..d9dd8fc7 100644
--- a/config/config_test.go
+++ b/config/config_test.go
@@ -265,6 +265,85 @@ services:
 	}
 }
 
+func TestParseAndValidateConfigBytesWithCustomAlertingConfig(t *testing.T) {
+	config, err := parseAndValidateConfigBytes([]byte(`
+alerting:
+  custom:
+    url: "https://example.com"
+    body: |
+      {
+        "text": "[ALERT_TRIGGERED_OR_RESOLVED]: [SERVICE_NAME] - [ALERT_DESCRIPTION]"
+      }
+services:
+  - name: twinnation
+    url: https://twinnation.org/actuator/health
+    alerts:
+      - type: custom
+    conditions:
+      - "[STATUS] == 200"
+`))
+	if err != nil {
+		t.Error("No error should've been returned")
+	}
+	if config == nil {
+		t.Fatal("Config shouldn't have been nil")
+	}
+	if config.Alerting == nil {
+		t.Fatal("config.Alerting shouldn't have been nil")
+	}
+	if config.Alerting.Custom == nil {
+		t.Fatal("PagerDuty alerting config shouldn't have been nil")
+	}
+	if !config.Alerting.Custom.IsValid() {
+		t.Fatal("Custom alerting config should've been valid")
+	}
+	if config.Alerting.Custom.Insecure {
+		t.Fatal("config.Alerting.Custom.Insecure shouldn't have been true")
+	}
+}
+
+func TestParseAndValidateConfigBytesWithCustomAlertingConfigThatHasInsecureSetToTrue(t *testing.T) {
+	config, err := parseAndValidateConfigBytes([]byte(`
+alerting:
+  custom:
+    url: "https://example.com"
+    method: "POST"
+    insecure: true
+    body: |
+      {
+        "text": "[ALERT_TRIGGERED_OR_RESOLVED]: [SERVICE_NAME] - [ALERT_DESCRIPTION]"
+      }
+services:
+  - name: twinnation
+    url: https://twinnation.org/actuator/health
+    alerts:
+      - type: custom
+    conditions:
+      - "[STATUS] == 200"
+`))
+	if err != nil {
+		t.Error("No error should've been returned")
+	}
+	if config == nil {
+		t.Fatal("Config shouldn't have been nil")
+	}
+	if config.Alerting == nil {
+		t.Fatal("config.Alerting shouldn't have been nil")
+	}
+	if config.Alerting.Custom == nil {
+		t.Fatal("PagerDuty alerting config shouldn't have been nil")
+	}
+	if !config.Alerting.Custom.IsValid() {
+		t.Error("Custom alerting config should've been valid")
+	}
+	if config.Alerting.Custom.Method != "POST" {
+		t.Error("config.Alerting.Custom.Method should've been POST")
+	}
+	if !config.Alerting.Custom.Insecure {
+		t.Error("config.Alerting.Custom.Insecure shouldn't have been true")
+	}
+}
+
 func TestParseAndValidateConfigBytesWithInvalidSecurityConfig(t *testing.T) {
 	defer func() { recover() }()
 	_, _ = parseAndValidateConfigBytes([]byte(`
diff --git a/watchdog/alerting.go b/watchdog/alerting.go
index 3e62b8a0..8806bf58 100644
--- a/watchdog/alerting.go
+++ b/watchdog/alerting.go
@@ -2,9 +2,10 @@ package watchdog
 
 import (
 	"encoding/json"
+	"log"
+
 	"github.com/TwinProduction/gatus/config"
 	"github.com/TwinProduction/gatus/core"
-	"log"
 )
 
 // HandleAlerting takes care of alerts to resolve and alerts to trigger based on result success or failure