diff --git a/CHANGELOG.next.asciidoc b/CHANGELOG.next.asciidoc
index 5f35daf8fd75..e66ae58f2c15 100644
--- a/CHANGELOG.next.asciidoc
+++ b/CHANGELOG.next.asciidoc
@@ -19,6 +19,7 @@ https://github.com/elastic/beats/compare/v7.0.0-alpha2...master[Check the HEAD d
 
 *Heartbeat*
 
+- Fix broken macOS ICMP python e2e test. {pull}29900[29900]
 - Only add monitor.status to browser events when summary. {pull}29460[29460]
 - Also add summary to journeys for which the synthetics runner crashes. {pull}29606[29606]
 
@@ -51,6 +52,7 @@ https://github.com/elastic/beats/compare/v7.0.0-alpha2...master[Check the HEAD d
 *Heartbeat*
 
 - Fix race condition in http monitors using `mode:all` that can cause crashes. {pull}29697[pull]
+- Fix broken ICMP availability check that prevented heartbeat from starting in rare cases. {pull}29413[pull]
 
 *Metricbeat*
 
@@ -83,6 +85,8 @@ https://github.com/elastic/beats/compare/v7.0.0-alpha2...master[Check the HEAD d
 
 *Heartbeat*
 
+- More errors are now visible in ES with new logic failing monitors later to ease debugging. {pull}29413[pull]
+
 
 *Metricbeat*
 
diff --git a/heartbeat/monitors/active/icmp/icmp.go b/heartbeat/monitors/active/icmp/icmp.go
index ef57cdbebae3..073660c259af 100644
--- a/heartbeat/monitors/active/icmp/icmp.go
+++ b/heartbeat/monitors/active/icmp/icmp.go
@@ -91,10 +91,6 @@ func (jf *jobFactory) checkConfig() error {
 }
 
 func (jf *jobFactory) makePlugin() (plugin2 plugin.Plugin, err error) {
-	if err := jf.loop.checkNetworkMode(jf.ipVersion); err != nil {
-		return plugin.Plugin{}, err
-	}
-
 	pingFactory := jf.pingIPFactory(&jf.config)
 
 	var j []jobs.Job
diff --git a/heartbeat/monitors/active/icmp/loop.go b/heartbeat/monitors/active/icmp/loop.go
index de4d0ef4dfc2..b29fa247f16d 100644
--- a/heartbeat/monitors/active/icmp/loop.go
+++ b/heartbeat/monitors/active/icmp/loop.go
@@ -23,7 +23,6 @@ import (
 )
 
 type ICMPLoop interface {
-	checkNetworkMode(mode string) error
 	ping(
 		addr *net.IPAddr,
 		timeout time.Duration,
diff --git a/heartbeat/monitors/active/icmp/stdloop.go b/heartbeat/monitors/active/icmp/stdloop.go
index 05858f5537fc..9f5f55439678 100644
--- a/heartbeat/monitors/active/icmp/stdloop.go
+++ b/heartbeat/monitors/active/icmp/stdloop.go
@@ -20,7 +20,6 @@ package icmp
 import (
 	"bytes"
 	"encoding/binary"
-	"errors"
 	"fmt"
 	"math/rand"
 	"net"
@@ -159,29 +158,6 @@ func newICMPLoop() (*stdICMPLoop, error) {
 	return l, nil
 }
 
-func (l *stdICMPLoop) checkNetworkMode(mode string) error {
-	ip4, ip6 := false, false
-	switch mode {
-	case "ip4":
-		ip4 = true
-	case "ip6":
-		ip6 = true
-	case "ip":
-		ip4, ip6 = true, true
-	default:
-		return fmt.Errorf("'%v' is not supported", mode)
-	}
-
-	if ip4 && l.conn4 == nil {
-		return errors.New("failed to initiate IPv4 support. Check log details for permission configuration")
-	}
-	if ip6 && l.conn6 == nil {
-		return errors.New("failed to initiate IPv6 support. Check log details for permission configuration")
-	}
-
-	return nil
-}
-
 func (l *stdICMPLoop) runICMPRecv(conn *icmp.PacketConn, proto int) {
 	for {
 		bytes := make([]byte, 512)
@@ -251,6 +227,14 @@ func (l *stdICMPLoop) ping(
 	timeout time.Duration,
 	interval time.Duration,
 ) (time.Duration, int, error) {
+	isIPv6 := addr.IP.To4() == nil
+	if isIPv6 && l.conn6 == nil {
+		return -1, -1, fmt.Errorf("cannot ping IPv6 address '%s', no IPv6 connection available", addr)
+	}
+	if !isIPv6 && l.conn4 == nil {
+		return -1, -1, fmt.Errorf("cannot ping IPv4 address '%s', no IPv4 connection available", addr)
+	}
+
 	var err error
 	toTimer := time.NewTimer(timeout)
 	defer toTimer.Stop()
@@ -379,7 +363,7 @@ func (l *stdICMPLoop) sendEchoRequest(addr *net.IPAddr) (*requestContext, error)
 
 	_, err := conn.WriteTo(encoded, addr)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("could not write to conn: %w", err)
 	}
 
 	ctx.ts = ts
diff --git a/heartbeat/monitors/factory_test.go b/heartbeat/monitors/factory_test.go
index c395050aaa1e..e4ff3589ccd8 100644
--- a/heartbeat/monitors/factory_test.go
+++ b/heartbeat/monitors/factory_test.go
@@ -149,7 +149,7 @@ func TestPreProcessors(t *testing.T) {
 }
 
 func TestDuplicateMonitorIDs(t *testing.T) {
-	serverMonConf := mockPluginConf(t, "custom", "@every 1ms", "http://example.net")
+	serverMonConf := mockPluginConf(t, "custom", "custom", "@every 1ms", "http://example.net")
 	badConf := mockBadPluginConf(t, "custom", "@every 1ms")
 	reg, built, closed := mockPluginsReg()
 	pipelineConnector := &MockPipelineConnector{}
@@ -190,8 +190,9 @@ func TestDuplicateMonitorIDs(t *testing.T) {
 	m1.Stop()
 	m2.Stop()
 
-	// 3 are counted as built, even the bad config
-	require.Equal(t, 3, built.Load())
+	// Two are counted as built. The bad config is missing a stdfield so it
+	// doesn't complete construction
+	require.Equal(t, 2, built.Load())
 	// Only 2 closes, because the bad config isn't closed
 	require.Equal(t, 2, closed.Load())
 }
diff --git a/heartbeat/monitors/mocks_test.go b/heartbeat/monitors/mocks_test.go
index 6d51791e3d72..720088db211f 100644
--- a/heartbeat/monitors/mocks_test.go
+++ b/heartbeat/monitors/mocks_test.go
@@ -99,24 +99,28 @@ func (pc *MockPipelineConnector) ConnectWith(beat.ClientConfig) (beat.Client, er
 	return c, nil
 }
 
-func mockEventMonitorValidator(id string) validator.Validator {
+func baseMockEventMonitorValidator(id string, name string, status string) validator.Validator {
 	var idMatcher isdef.IsDef
 	if id == "" {
 		idMatcher = isdef.IsStringMatching(regexp.MustCompile(`^auto-test-.*`))
 	} else {
 		idMatcher = isdef.IsEqual(id)
 	}
+	return lookslike.MustCompile(map[string]interface{}{
+		"monitor": map[string]interface{}{
+			"id":          idMatcher,
+			"name":        name,
+			"type":        "test",
+			"duration.us": isdef.IsDuration,
+			"status":      status,
+			"check_group": isdef.IsString,
+		},
+	})
+}
+
+func mockEventMonitorValidator(id string, name string) validator.Validator {
 	return lookslike.Strict(lookslike.Compose(
-		lookslike.MustCompile(map[string]interface{}{
-			"monitor": map[string]interface{}{
-				"id":          idMatcher,
-				"name":        "",
-				"type":        "test",
-				"duration.us": isdef.IsDuration,
-				"status":      "up",
-				"check_group": isdef.IsString,
-			},
-		}),
+		baseMockEventMonitorValidator(id, name, "up"),
 		hbtestllext.MonitorTimespanValidator,
 		hbtest.SummaryChecks(1, 0),
 		lookslike.MustCompile(mockEventCustomFields()),
@@ -151,15 +155,19 @@ func mockPluginBuilder() (plugin.PluginFactory, *atomic.Int, *atomic.Int) {
 				unpacked := struct {
 					URLs []string `config:"urls" validate:"required"`
 				}{}
-				err := config.Unpack(&unpacked)
-				if err != nil {
-					return plugin.Plugin{}, err
-				}
-				j, err := createMockJob()
+
+				// track all closes, even on error
 				closer := func() error {
 					closed.Inc()
 					return nil
 				}
+
+				err := config.Unpack(&unpacked)
+				if err != nil {
+					return plugin.Plugin{DoClose: closer}, err
+				}
+				j, err := createMockJob()
+
 				return plugin.Plugin{Jobs: j, DoClose: closer, Endpoints: 1}, err
 			},
 			Stats: plugin.NewPluginCountersRecorder("test", reg)},
@@ -174,13 +182,15 @@ func mockPluginsReg() (p *plugin.PluginsReg, built *atomic.Int, closed *atomic.I
 	return reg, built, closed
 }
 
-func mockPluginConf(t *testing.T, id string, schedule string, url string) *common.Config {
+func mockPluginConf(t *testing.T, id string, name string, schedule string, url string) *common.Config {
 	confMap := map[string]interface{}{
 		"type":     "test",
 		"urls":     []string{url},
 		"schedule": schedule,
+		"name":     name,
 	}
 
+	// Optional to let us simulate this key missing
 	if id != "" {
 		confMap["id"] = id
 	}
@@ -197,7 +207,6 @@ func mockBadPluginConf(t *testing.T, id string, schedule string) *common.Config
 	confMap := map[string]interface{}{
 		"type":        "test",
 		"notanoption": []string{"foo"},
-		"schedule":    schedule,
 	}
 
 	if id != "" {
@@ -210,8 +219,6 @@ func mockBadPluginConf(t *testing.T, id string, schedule string) *common.Config
 	return conf
 }
 
-// mockInvalidPlugin conf returns a config that invalid at the basic level of
-// what's expected in heartbeat, i.e. no type.
 func mockInvalidPluginConf(t *testing.T) *common.Config {
 	confMap := map[string]interface{}{
 		"hoeutnheou": "oueanthoue",
@@ -222,3 +229,17 @@ func mockInvalidPluginConf(t *testing.T) *common.Config {
 
 	return conf
 }
+
+func mockInvalidPluginConfWithStdFields(t *testing.T, id string, name string, schedule string) *common.Config {
+	confMap := map[string]interface{}{
+		"type":     "test",
+		"id":       id,
+		"name":     name,
+		"schedule": schedule,
+	}
+
+	conf, err := common.NewConfigFrom(confMap)
+	require.NoError(t, err)
+
+	return conf
+}
diff --git a/heartbeat/monitors/monitor.go b/heartbeat/monitors/monitor.go
index 669579e31aa0..91a6a881d848 100644
--- a/heartbeat/monitors/monitor.go
+++ b/heartbeat/monitors/monitor.go
@@ -163,13 +163,26 @@ func newMonitorUnsafe(
 		return p.Close()
 	}
 
-	wrappedJobs := wrappers.WrapCommon(p.Jobs, m.stdFields)
-	m.endpoints = p.Endpoints
-
+	// If we've hit an error at this point, still run on schedule, but always return an error.
+	// This way the error is clearly communicated through to kibana.
+	// Since the error is not recoverable in these instances, the user will need to reconfigure
+	// the monitor, which will destroy and recreate it in heartbeat, thus clearing this error.
+	//
+	// Note: we do this at this point, and no earlier, because at a minimum we need the
+	// standard monitor fields (id, name and schedule) to deliver an error to kibana in a way
+	// that it can render.
 	if err != nil {
-		return m, fmt.Errorf("job err %v", err)
+		// Note, needed to hoist err to this scope, not just to add a prefix
+		fullErr := fmt.Errorf("job could not be initialized: %s", err)
+		// A placeholder job that always returns an error
+		p.Jobs = []jobs.Job{func(event *beat.Event) ([]jobs.Job, error) {
+			return nil, fullErr
+		}}
 	}
 
+	wrappedJobs := wrappers.WrapCommon(p.Jobs, m.stdFields)
+	m.endpoints = p.Endpoints
+
 	m.configuredJobs, err = m.makeTasks(config, wrappedJobs)
 	if err != nil {
 		return m, err
diff --git a/heartbeat/monitors/monitor_test.go b/heartbeat/monitors/monitor_test.go
index bbcd5b9b74c5..8184a867eaea 100644
--- a/heartbeat/monitors/monitor_test.go
+++ b/heartbeat/monitors/monitor_test.go
@@ -25,19 +25,49 @@ import (
 	"github.com/stretchr/testify/require"
 
 	"github.com/elastic/beats/v7/heartbeat/scheduler"
+	"github.com/elastic/beats/v7/libbeat/common"
 	"github.com/elastic/beats/v7/libbeat/monitoring"
+	"github.com/elastic/go-lookslike"
+	"github.com/elastic/go-lookslike/isdef"
 	"github.com/elastic/go-lookslike/testslike"
+	"github.com/elastic/go-lookslike/validator"
 )
 
-func TestMonitor(t *testing.T) {
-	serverMonConf := mockPluginConf(t, "", "@every 1ms", "http://example.net")
+// TestMonitorBasic tests a basic config
+func TestMonitorBasic(t *testing.T) {
+	testMonitorConfig(
+		t,
+		mockPluginConf(t, "myId", "myName", "@every 1ms", "http://example.net"),
+		mockEventMonitorValidator("myId", "myName"),
+	)
+}
+
+// TestMonitorBasic tests a config that errors out at plugin creation, but still has stdfields defined.
+// This should cause the monitor to run, but only produce error documents
+func TestMonitorCfgError(t *testing.T) {
+	testMonitorConfig(
+		t,
+		mockInvalidPluginConfWithStdFields(t, "invalidTestId", "invalidTestName", "@every 10s"),
+		lookslike.Compose(
+			baseMockEventMonitorValidator("invalidTestId", "invalidTestName", "down"),
+			lookslike.MustCompile(common.MapStr{
+				"error": common.MapStr{
+					"message": isdef.IsStringContaining("missing required field"),
+					"type":    "io",
+				},
+			}),
+		),
+	)
+}
+
+func testMonitorConfig(t *testing.T, conf *common.Config, eventValidator validator.Validator) {
 	reg, built, closed := mockPluginsReg()
 	pipelineConnector := &MockPipelineConnector{}
 
 	sched := scheduler.Create(1, monitoring.NewRegistry(), time.Local, nil, false)
 	defer sched.Stop()
 
-	mon, err := newMonitor(serverMonConf, reg, pipelineConnector, sched.Add, nil, false)
+	mon, err := newMonitor(conf, reg, pipelineConnector, sched.Add, nil, false)
 	require.NoError(t, err)
 
 	mon.Start()
@@ -56,7 +86,7 @@ func TestMonitor(t *testing.T) {
 			pcClient.Close()
 
 			for _, event := range pcClient.Publishes() {
-				testslike.Test(t, mockEventMonitorValidator(""), event.Fields)
+				testslike.Test(t, eventValidator, event.Fields)
 			}
 		} else {
 			// Let's yield this goroutine so we don't spin
diff --git a/heartbeat/monitors/stdfields/stdfields.go b/heartbeat/monitors/stdfields/stdfields.go
index f09161c2adf0..92e5bc4bb90f 100644
--- a/heartbeat/monitors/stdfields/stdfields.go
+++ b/heartbeat/monitors/stdfields/stdfields.go
@@ -18,10 +18,9 @@
 package stdfields
 
 import (
+	"fmt"
 	"time"
 
-	"github.com/pkg/errors"
-
 	"github.com/elastic/beats/v7/heartbeat/scheduler/schedule"
 	"github.com/elastic/beats/v7/libbeat/common"
 )
@@ -46,7 +45,7 @@ func ConfigToStdMonitorFields(config *common.Config) (StdMonitorFields, error) {
 	mpi := StdMonitorFields{Enabled: true}
 
 	if err := config.Unpack(&mpi); err != nil {
-		return mpi, errors.Wrap(err, "error unpacking monitor plugin config")
+		return mpi, fmt.Errorf("error unpacking monitor plugin config: %w", err)
 	}
 
 	// Use `service_name` if `service.name` is unspecified
diff --git a/heartbeat/monitors/task.go b/heartbeat/monitors/task.go
index 11b013a98717..a7f1848b3aef 100644
--- a/heartbeat/monitors/task.go
+++ b/heartbeat/monitors/task.go
@@ -108,7 +108,7 @@ func runPublishJob(job jobs.Job, client *WrappedClient) []scheduler.TaskFunc {
 
 	conts, err := job(event)
 	if err != nil {
-		logp.Err("Job %v failed with: ", err)
+		logp.Err("Job failed with: %s", err)
 	}
 
 	hasContinuations := len(conts) > 0
diff --git a/heartbeat/tests/system/test_icmp.py b/heartbeat/tests/system/test_icmp.py
index 7f61a7430f88..f7be72e89f42 100644
--- a/heartbeat/tests/system/test_icmp.py
+++ b/heartbeat/tests/system/test_icmp.py
@@ -6,6 +6,7 @@
 import sys
 import time
 import unittest
+import re
 from beat.beat import INTEGRATION_TESTS
 from elasticsearch import Elasticsearch
 from heartbeat import BaseTest
@@ -35,17 +36,10 @@ def test_base(self):
 
         proc = self.start_beat()
 
-        def has_started_message(): return self.log_contains("ICMP loop successfully initialized")
-
-        def has_failed_message(): return self.log_contains("Failed to initialize ICMP loop")
-
-        # We don't know if the system tests are running is configured to support or not support ping, but we can at least check that the ICMP loop
-        # was initiated. In the future we should start up VMs with the correct perms configured and be more specific. In addition to that
-        # we should run pings on those machines and make sure they work.
-        self.wait_until(lambda: has_started_message() or has_failed_message(), 30)
-
-        if has_failed_message():
-            proc.check_kill_and_wait(1)
-        else:
-            # Check that documents are moving through
-            self.wait_until(lambda: self.output_has(lines=1))
+        # because we have no way of knowing if the current environment has the ability to do ICMP pings
+        # we are instead asserting the monitor's status via the output and checking for errors where appropriate
+        self.wait_until(lambda: self.output_has(lines=1))
+        output = self.read_output()
+        monitor_status = output[0]["monitor.status"]
+        assert monitor_status == "up" or monitor_status == "down"
+        assert output[0]["monitor.type"] == "icmp"
diff --git a/x-pack/heartbeat/.gitignore b/x-pack/heartbeat/.gitignore
new file mode 100644
index 000000000000..8af6c73dc612
--- /dev/null
+++ b/x-pack/heartbeat/.gitignore
@@ -0,0 +1 @@
+.synthetics