diff --git a/data/data/bootstrap/files/usr/local/bin/bootkube.sh.template b/data/data/bootstrap/files/usr/local/bin/bootkube.sh.template
index 7e928b90229..51dcb8ae8bd 100755
--- a/data/data/bootstrap/files/usr/local/bin/bootkube.sh.template
+++ b/data/data/bootstrap/files/usr/local/bin/bootkube.sh.template
@@ -5,6 +5,7 @@ set -euoE pipefail ## -E option will cause functions to inherit trap
 
 . /usr/local/bin/release-image.sh
 . /usr/local/bin/bootstrap-cluster-gather.sh
+. /usr/local/bin/bootstrap-verify-api-server-urls.sh
 
 mkdir --parents /etc/kubernetes/{manifests,bootstrap-configs,bootstrap-manifests}
 
@@ -356,6 +357,19 @@ then
     record_service_stage_success
 fi
 
+# Check if the API and API_INT Server URLs can be resolved and reached.
+echo "Check if API and API-Int URLs are resolvable during bootstrap"
+API_SERVER_URL="{{.APIServerURL}}"
+API_INT_SERVER_URL="{{.APIIntServerURL}}" 
+
+if [[ ! -z "${API_SERVER_URL}" ]] ; then
+    check_url "API_URL" "${API_SERVER_URL}"
+fi
+
+if [[ ! -z "${API_INT_SERVER_URL}" ]] ; then
+    check_url "API_INT_URL" "${API_INT_SERVER_URL}"
+fi
+
 if [ ! -f cco-bootstrap.done ]
 then
     record_service_stage_start "cco-bootstrap"
diff --git a/data/data/bootstrap/files/usr/local/bin/bootstrap-verify-api-server-urls.sh b/data/data/bootstrap/files/usr/local/bin/bootstrap-verify-api-server-urls.sh
new file mode 100644
index 00000000000..8805221a12b
--- /dev/null
+++ b/data/data/bootstrap/files/usr/local/bin/bootstrap-verify-api-server-urls.sh
@@ -0,0 +1,82 @@
+#!/usr/bin/env bash
+
+# shellcheck disable=SC1091
+. /usr/local/bin/bootstrap-service-record.sh
+
+# This functions expects 2 arguments:
+# 1. name of the URL
+# 2. The value of the URL
+function resolve_url() {
+    unset IPS
+    unset IP
+    IPS=$(dig "${2}" +short)
+    if [[ ! -z "${IPS}" ]] ; then
+        echo "Successfully resolved ${1} ${2}"
+        # dig returns multiple IPs. Check if the
+        # first IP is reachable.
+        ip_arr=""
+        readarray ip_arr -t <<<"${IPS}"
+        IP="$(echo "${ip_arr[0]}" | tr -d '\n')"
+        return 0
+    else
+        echo "Unable to resolve ${1} ${2}"
+        return 1
+    fi
+}
+
+# This functions expects 2 arguments:
+# 1. name of the URL
+# 2. URL to validate
+function validate_url() {
+    if [[ $(curl --head -k --silent --fail --write-out "%{http_code}\\n" "${2}" -o /dev/null) == 200 ]]; then
+        echo "Success while trying to reach ${1}'s https endpoint at ${2}"
+        return 0
+    else
+        echo "Unable to reach ${1}'s https endpoint at ${2}"
+        return 1
+    fi
+}
+
+function check_url() {
+    if [[ -z "${1}" ]] || [[ -z "${2}" ]]; then
+        echo "Usage: check_url <API_URL or API_INT URL> <URL that needs to be verified>"
+        return
+    fi
+
+    local URL_TYPE=${1}
+    local SERVER_URL=${2}
+
+    if [[ ${URL_TYPE} != API_URL ]] && [[ ${URL_TYPE} != API_INT_URL ]]; then
+        echo "Usage: check_url <API_URL or API_INT URL> <URL that needs to be verified>"
+        return
+    fi
+
+    echo "Checking validity of ${SERVER_URL} of type ${URL_TYPE}"
+
+    if [[ "${URL_TYPE}" = "API_URL" ]]; then
+        local URL_STAGE_NAME="check-api-url"
+    else 
+        local URL_STAGE_NAME="check-api-int-url"
+    fi
+
+    echo "Starting stage ${URL_STAGE_NAME}"
+    record_service_stage_start ${URL_STAGE_NAME}
+    if resolve_url "$URL_TYPE" "$SERVER_URL"; then
+        record_service_stage_success
+    else
+        record_service_stage_failure
+        # We do not want to stop bootkube service due to this failure.
+        # So not returning failure at this point.
+        return
+    fi
+
+    CURL_URL="https://${IP}:6443/version"
+
+    record_service_stage_start ${URL_STAGE_NAME}
+    if validate_url "$URL_TYPE" "$CURL_URL"; then
+        record_service_stage_success
+    else
+        echo "It might be too early for the ${CURL_URL} to be available."
+        record_service_stage_failure
+    fi
+}
diff --git a/pkg/asset/ignition/bootstrap/common.go b/pkg/asset/ignition/bootstrap/common.go
index c0b76f8808e..1d261aeb6dd 100644
--- a/pkg/asset/ignition/bootstrap/common.go
+++ b/pkg/asset/ignition/bootstrap/common.go
@@ -80,6 +80,8 @@ type bootstrapTemplateData struct {
 	UseIPv6ForNodeIP      bool
 	IsOKD                 bool
 	BootstrapNodeIP       string
+	APIServerURL          string
+	APIIntServerURL       string
 }
 
 // platformTemplateData is the data to use to replace values in bootstrap
@@ -285,6 +287,9 @@ func (a *Common) getTemplateData(dependencies asset.Parents, bootstrapInPlace bo
 	if bootstrapInPlace {
 		bootstrapInPlaceConfig = installConfig.Config.BootstrapInPlace
 	}
+
+	apiURL := fmt.Sprintf("api.%s", installConfig.Config.ClusterDomain())
+	apiIntURL := fmt.Sprintf("api-int.%s", installConfig.Config.ClusterDomain())
 	return &bootstrapTemplateData{
 		AdditionalTrustBundle: installConfig.Config.AdditionalTrustBundle,
 		FIPS:                  installConfig.Config.FIPS,
@@ -301,6 +306,8 @@ func (a *Common) getTemplateData(dependencies asset.Parents, bootstrapInPlace bo
 		UseIPv6ForNodeIP:      APIIntVIPonIPv6,
 		IsOKD:                 installConfig.Config.IsOKD(),
 		BootstrapNodeIP:       bootstrapNodeIP,
+		APIServerURL:          apiURL,
+		APIIntServerURL:       apiIntURL,
 	}
 }
 
diff --git a/pkg/gather/service/analyze.go b/pkg/gather/service/analyze.go
index 83e98dc2784..ea851c6f7ff 100644
--- a/pkg/gather/service/analyze.go
+++ b/pkg/gather/service/analyze.go
@@ -72,14 +72,20 @@ func analyzeGatherBundle(bundleFile io.Reader) error {
 	}
 
 	analysisChecks := []struct {
-		name  string
-		check func(analysis) bool
+		name     string
+		check    func(analysis) bool
+		optional bool
 	}{
-		{name: "release-image", check: checkReleaseImageDownload},
+		{name: "release-image", check: checkReleaseImageDownload, optional: false},
+		{name: "bootkube", check: checkAPIURLs, optional: false},
 	}
 	for _, check := range analysisChecks {
 		a := serviceAnalyses[check.name]
 		if a.starts == 0 {
+			if check.optional {
+				logrus.Infof("The bootstrap machine did not execute the %s.service systemd unit", check.name)
+				break
+			}
 			logrus.Errorf("The bootstrap machine did not execute the %s.service systemd unit", check.name)
 			break
 		}
@@ -100,6 +106,23 @@ func checkReleaseImageDownload(a analysis) bool {
 	return false
 }
 
+// bootstrap-verify-api-servel-urls.sh is currently running as part of the bootkube service.
+// And the verification of the API and API-Int URLs are the only stage where a failure is
+// currently reported. So, here we are able to conclude that a failure corresponds to a
+// failure to resolve either the API URL or API-Int URL or both. If that changes and if
+// any other stage in the bootkube service starts reporting a failure, we need to revisit
+// this. At that point verification of the URLs could be moved to its own service.
+func checkAPIURLs(a analysis) bool {
+	if a.successful {
+		return true
+	}
+	// Note: Even when there is a stage failure, we are not returning false here. That is
+	// intentional because we donot want to report this as an error in the "analyze" output.
+	logrus.Warn("The bootstrap machine is unable to resolve API and/or API-Int Server URLs")
+	a.logLastError()
+	return true
+}
+
 type analysis struct {
 	// starts is the number of times that the service started
 	starts int
diff --git a/pkg/gather/service/analyze_test.go b/pkg/gather/service/analyze_test.go
index e44d3759afd..cdee040d84a 100644
--- a/pkg/gather/service/analyze_test.go
+++ b/pkg/gather/service/analyze_test.go
@@ -11,6 +11,41 @@ import (
 	"github.com/stretchr/testify/assert"
 )
 
+func generateSuccessOutput(stage string) string {
+	return `[
+{"phase":"service start"},
+{"phase":"stage start", "stage":"` + stage + `"},
+{"phase":"stage end", "stage":"` + stage + `", "result":"success"},
+{"phase":"service end", "result":"success"}
+]`
+}
+
+func generateFailureOutput(stage string) string {
+	return `[
+{"phase":"service start"},
+{"phase":"stage start", "stage":"` + stage + `"},
+{"phase":"stage end", "stage":"` + stage + `", "result":"failure", "errorMessage":"Line 1\nLine 2\nLine 3"}
+]`
+}
+
+func failedReleaseImage() []logrus.Entry {
+	return []logrus.Entry{
+		{Level: logrus.ErrorLevel, Message: "The bootstrap machine failed to download the release image"},
+		{Level: logrus.InfoLevel, Message: "Line 1"},
+		{Level: logrus.InfoLevel, Message: "Line 2"},
+		{Level: logrus.InfoLevel, Message: "Line 3"},
+	}
+}
+
+func failedURLChecks() []logrus.Entry {
+	return []logrus.Entry{
+		{Level: logrus.WarnLevel, Message: "The bootstrap machine is unable to resolve API and/or API-Int Server URLs"},
+		{Level: logrus.InfoLevel, Message: "Line 1"},
+		{Level: logrus.InfoLevel, Message: "Line 2"},
+		{Level: logrus.InfoLevel, Message: "Line 3"},
+	}
+}
+
 func TestAnalyzeGatherBundle(t *testing.T) {
 	cases := []struct {
 		name           string
@@ -33,42 +68,60 @@ func TestAnalyzeGatherBundle(t *testing.T) {
 			},
 		},
 		{
-			name: "release-image successful",
+			name: "bootkube not started",
 			files: map[string]string{
-				"log-bundle/bootstrap/services/release-image.json": `[
-{"phase":"service start"},
-{"phase":"stage start", "stage":"pull-release-image"},
-{"phase":"stage end", "stage":"pull-release-image", "result":"success"},
-{"phase":"service end", "result":"success"}
-]`,
+				"log-bundle/bootstrap/services/release-image.json": generateSuccessOutput("pull-release-image"),
+				"log-bundle/bootstrap/services/bootkube.json":      "[]",
+			},
+			expectedOutput: []logrus.Entry{
+				{Level: logrus.ErrorLevel, Message: "The bootstrap machine did not execute the bootkube.service systemd unit"},
 			},
 		},
 		{
-			name: "release-image successful bootstrap-in-place",
+			name: "release-image and API Server URL successful",
 			files: map[string]string{
-				"log-bundle/log-bundle-bootstrap/bootstrap/services/release-image.json": `[
-{"phase":"service start"},
-{"phase":"stage start", "stage":"pull-release-image"},
-{"phase":"stage end", "stage":"pull-release-image", "result":"success"},
-{"phase":"service end", "result":"success"}
-]`,
+				"log-bundle/bootstrap/services/release-image.json": generateSuccessOutput("pull-release-image"),
+				"log-bundle/bootstrap/services/bootkube.json":      generateSuccessOutput("check-api-url"),
 			},
 		},
 		{
-			name: "release-image failed",
+			name: "release-image and API Server URL successful bootstrap-in-place",
 			files: map[string]string{
-				"log-bundle/bootstrap/services/release-image.json": `[
-{"phase":"service start"},
-{"phase":"stage start", "stage":"pull-release-image"},
-{"phase":"stage end", "stage":"pull-release-image", "result":"failure", "errorMessage":"Line 1\nLine 2\nLine 3"}
-]`,
+				"log-bundle/log-bundle-bootstrap/bootstrap/services/release-image.json": generateSuccessOutput("pull-release-image"),
+				"log-bundle/bootstrap/services/bootkube.json":                           generateSuccessOutput("check-api-url"),
 			},
-			expectedOutput: []logrus.Entry{
-				{Level: logrus.ErrorLevel, Message: "The bootstrap machine failed to download the release image"},
-				{Level: logrus.InfoLevel, Message: "Line 1"},
-				{Level: logrus.InfoLevel, Message: "Line 2"},
-				{Level: logrus.InfoLevel, Message: "Line 3"},
+		},
+		{
+			name: "only release-image failed",
+			files: map[string]string{
+				"log-bundle/bootstrap/services/release-image.json": generateFailureOutput("pull-release-image"),
+				"log-bundle/bootstrap/services/bootkube.json":      generateSuccessOutput("check-api-url"),
 			},
+			expectedOutput: failedReleaseImage(),
+		},
+		{
+			name: "API Server URL failed",
+			files: map[string]string{
+				"log-bundle/log-bundle-bootstrap/bootstrap/services/release-image.json": generateSuccessOutput("pull-release-image"),
+				"log-bundle/bootstrap/services/bootkube.json":                           generateFailureOutput("check-api-url"),
+			},
+			expectedOutput: failedURLChecks(),
+		},
+		{
+			name: "API-INT Server URL failed",
+			files: map[string]string{
+				"log-bundle/log-bundle-bootstrap/bootstrap/services/release-image.json": generateSuccessOutput("pull-release-image"),
+				"log-bundle/bootstrap/services/bootkube.json":                           generateFailureOutput("check-api-int-url"),
+			},
+			expectedOutput: failedURLChecks(),
+		},
+		{
+			name: "both release-image and API Server URLs failed",
+			files: map[string]string{
+				"log-bundle/log-bundle-bootstrap/bootstrap/services/release-image.json": generateFailureOutput("pull-release-image"),
+				"log-bundle/bootstrap/services/bootkube.json":                           generateFailureOutput("check-api-url"),
+			},
+			expectedOutput: failedReleaseImage(),
 		},
 		{
 			name: "empty release-image.json",
@@ -80,6 +133,17 @@ func TestAnalyzeGatherBundle(t *testing.T) {
 				{Level: logrus.ErrorLevel, Message: "The bootstrap machine did not execute the release-image.service systemd unit"},
 			},
 		},
+		{
+			name: "empty bootkube.json",
+			files: map[string]string{
+				"log-bundle/bootstrap/services/release-image.json": generateSuccessOutput("pull-release-image"),
+				"log-bundle/bootstrap/services/bootkube.json":      "",
+			},
+			expectedOutput: []logrus.Entry{
+				{Level: logrus.InfoLevel, Message: "Could not analyze the bootkube.service: service entries file does not begin with a token: EOF"},
+				{Level: logrus.ErrorLevel, Message: "The bootstrap machine did not execute the bootkube.service systemd unit"},
+			},
+		},
 		{
 			name: "malformed release-image.json",
 			files: map[string]string{
@@ -90,6 +154,17 @@ func TestAnalyzeGatherBundle(t *testing.T) {
 				{Level: logrus.ErrorLevel, Message: "The bootstrap machine did not execute the release-image.service systemd unit"},
 			},
 		},
+		{
+			name: "malformed bootkube.json",
+			files: map[string]string{
+				"log-bundle/bootstrap/services/release-image.json": generateSuccessOutput("pull-release-image"),
+				"log-bundle/bootstrap/services/bootkube.json":      "{}",
+			},
+			expectedOutput: []logrus.Entry{
+				{Level: logrus.InfoLevel, Message: "Could not analyze the bootkube.service: service entries file does not begin with an array"},
+				{Level: logrus.ErrorLevel, Message: "The bootstrap machine did not execute the bootkube.service systemd unit"},
+			},
+		},
 	}
 	for _, tc := range cases {
 		t.Run(tc.name, func(t *testing.T) {