diff --git a/command/healthcheck/pki_allow_acme_headers.go b/command/healthcheck/pki_allow_acme_headers.go
new file mode 100644
index 000000000..2015ac276
--- /dev/null
+++ b/command/healthcheck/pki_allow_acme_headers.go
@@ -0,0 +1,155 @@
+// Copyright (c) HashiCorp, Inc.
+// SPDX-License-Identifier: MPL-2.0
+
+package healthcheck
+
+import (
+	"fmt"
+	"strings"
+
+	"github.com/hashicorp/go-secure-stdlib/parseutil"
+	"github.com/hashicorp/go-secure-stdlib/strutil"
+	"github.com/hashicorp/vault/sdk/logical"
+)
+
+type AllowAcmeHeaders struct {
+	Enabled            bool
+	UnsupportedVersion bool
+
+	TuneFetcher *PathFetch
+	TuneData    map[string]interface{}
+
+	AcmeConfigFetcher *PathFetch
+}
+
+func NewAllowAcmeHeaders() Check {
+	return &AllowAcmeHeaders{}
+}
+
+func (h *AllowAcmeHeaders) Name() string {
+	return "allow_acme_headers"
+}
+
+func (h *AllowAcmeHeaders) IsEnabled() bool {
+	return h.Enabled
+}
+
+func (h *AllowAcmeHeaders) DefaultConfig() map[string]interface{} {
+	return map[string]interface{}{}
+}
+
+func (h *AllowAcmeHeaders) LoadConfig(config map[string]interface{}) error {
+	enabled, err := parseutil.ParseBool(config["enabled"])
+	if err != nil {
+		return fmt.Errorf("error parsing %v.enabled: %w", h.Name(), err)
+	}
+	h.Enabled = enabled
+
+	return nil
+}
+
+func (h *AllowAcmeHeaders) FetchResources(e *Executor) error {
+	var err error
+	h.AcmeConfigFetcher, err = e.FetchIfNotFetched(logical.ReadOperation, "/{{mount}}/config/acme")
+	if err != nil {
+		return err
+	}
+
+	if h.AcmeConfigFetcher.IsUnsupportedPathError() {
+		h.UnsupportedVersion = true
+	}
+
+	_, h.TuneFetcher, h.TuneData, err = fetchMountTune(e, func() {
+		h.UnsupportedVersion = true
+	})
+	if err != nil {
+		return err
+	}
+
+	return nil
+}
+
+func (h *AllowAcmeHeaders) Evaluate(e *Executor) ([]*Result, error) {
+	if h.UnsupportedVersion {
+		ret := Result{
+			Status:   ResultInvalidVersion,
+			Endpoint: h.AcmeConfigFetcher.Path,
+			Message:  "This health check requires Vault 1.14+ but an earlier version of Vault Server was contacted, preventing this health check from running.",
+		}
+		return []*Result{&ret}, nil
+	}
+
+	if h.AcmeConfigFetcher.IsSecretPermissionsError() {
+		msg := "Without read access to ACME configuration, this health check is unable to function."
+		return craftInsufficientPermissionResult(e, h.AcmeConfigFetcher.Path, msg), nil
+	}
+
+	acmeEnabled, err := isAcmeEnabled(h.AcmeConfigFetcher)
+	if err != nil {
+		return nil, err
+	}
+
+	if !acmeEnabled {
+		ret := Result{
+			Status:   ResultNotApplicable,
+			Endpoint: h.AcmeConfigFetcher.Path,
+			Message:  "ACME is not enabled, no additional response headers required.",
+		}
+		return []*Result{&ret}, nil
+	}
+
+	if h.TuneFetcher.IsSecretPermissionsError() {
+		msg := "Without access to mount tune information, this health check is unable to function."
+		return craftInsufficientPermissionResult(e, h.TuneFetcher.Path, msg), nil
+	}
+
+	resp, err := StringList(h.TuneData["allowed_response_headers"])
+	if err != nil {
+		return nil, fmt.Errorf("unable to parse value from server for allowed_response_headers: %w", err)
+	}
+
+	requiredResponseHeaders := []string{"Replay-Nonce", "Link", "Location"}
+	foundResponseHeaders := []string{}
+	for _, param := range resp {
+		for _, reqHeader := range requiredResponseHeaders {
+			if strings.EqualFold(param, reqHeader) {
+				foundResponseHeaders = append(foundResponseHeaders, reqHeader)
+				break
+			}
+		}
+	}
+
+	foundAllHeaders := strutil.EquivalentSlices(requiredResponseHeaders, foundResponseHeaders)
+
+	if !foundAllHeaders {
+		ret := Result{
+			Status:   ResultWarning,
+			Endpoint: "/sys/mounts/{{mount}}/tune",
+			Message:  "Mount hasn't enabled 'Replay-Nonce', 'Link', 'Location' response headers, these are required for ACME to function.",
+		}
+		return []*Result{&ret}, nil
+	}
+
+	ret := Result{
+		Status:   ResultOK,
+		Endpoint: "/sys/mounts/{{mount}}/tune",
+		Message:  "Mount has enabled 'Replay-Nonce', 'Link', 'Location' response headers.",
+	}
+	return []*Result{&ret}, nil
+}
+
+func craftInsufficientPermissionResult(e *Executor, path, errorMsg string) []*Result {
+	ret := Result{
+		Status:   ResultInsufficientPermissions,
+		Endpoint: path,
+		Message:  errorMsg,
+	}
+
+	if e.Client.Token() == "" {
+		ret.Message = "No token available so unable read the tune endpoint for this mount. " + ret.Message
+	} else {
+		ret.Message = "This token lacks permission to read the tune endpoint for this mount. " + ret.Message
+	}
+
+	return []*Result{&ret}
+}
diff --git a/command/healthcheck/pki_enable_acme_issuance.go b/command/healthcheck/pki_enable_acme_issuance.go
new file mode 100644
index 000000000..986165d0e
--- /dev/null
+++ b/command/healthcheck/pki_enable_acme_issuance.go
@@ -0,0 +1,237 @@
+// Copyright (c) HashiCorp, Inc.
+// SPDX-License-Identifier: MPL-2.0
+
+package healthcheck
+
+import (
+	"bytes"
+	"context"
+	"crypto/tls"
+	"fmt"
+	"net/http"
+	"net/url"
+
+	"github.com/hashicorp/go-secure-stdlib/parseutil"
+	"github.com/hashicorp/vault/sdk/logical"
+
+	"golang.org/x/crypto/acme"
+)
+
+type EnableAcmeIssuance struct {
+	Enabled            bool
+	UnsupportedVersion bool
+
+	AcmeConfigFetcher    *PathFetch
+	ClusterConfigFetcher *PathFetch
+	TotalIssuers         int
+	RootIssuers          int
+}
+
+func NewEnableAcmeIssuance() Check {
+	return &EnableAcmeIssuance{}
+}
+
+func (h *EnableAcmeIssuance) Name() string {
+	return "enable_acme_issuance"
+}
+
+func (h *EnableAcmeIssuance) IsEnabled() bool {
+	return h.Enabled
+}
+
+func (h *EnableAcmeIssuance) DefaultConfig() map[string]interface{} {
+	return map[string]interface{}{}
+}
+
+func (h *EnableAcmeIssuance) LoadConfig(config map[string]interface{}) error {
+	enabled, err := parseutil.ParseBool(config["enabled"])
+	if err != nil {
+		return fmt.Errorf("error parsing %v.enabled: %w", h.Name(), err)
+	}
+	h.Enabled = enabled
+
+	return nil
+}
+
+func (h *EnableAcmeIssuance) FetchResources(e *Executor) error {
+	var err error
+	h.AcmeConfigFetcher, err = e.FetchIfNotFetched(logical.ReadOperation, "/{{mount}}/config/acme")
+	if err != nil {
+		return err
+	}
+
+	if h.AcmeConfigFetcher.IsUnsupportedPathError() {
+		h.UnsupportedVersion = true
+	}
+
+	h.ClusterConfigFetcher, err = e.FetchIfNotFetched(logical.ReadOperation, "/{{mount}}/config/cluster")
+	if err != nil {
+		return err
+	}
+
+	if h.ClusterConfigFetcher.IsUnsupportedPathError() {
+		h.UnsupportedVersion = true
+	}
+
+	h.TotalIssuers, h.RootIssuers, err = doesMountContainOnlyRootIssuers(e)
+
+	return nil
+}
+
+func doesMountContainOnlyRootIssuers(e *Executor) (int, int, error) {
+	exit, _, issuers, err := pkiFetchIssuersList(e, func() {})
+	if exit || err != nil {
+		return 0, 0, err
+	}
+
+	totalIssuers := 0
+	rootIssuers := 0
+
+	for _, issuer := range issuers {
+		skip, _, cert, err := pkiFetchIssuer(e, issuer, func() {})
+
+		if skip || err != nil {
+			if err != nil {
+				return 0, 0, err
+			}
+			continue
+		}
+		totalIssuers++
+
+		if !bytes.Equal(cert.RawSubject, cert.RawIssuer) {
+			continue
+		}
+		if err := cert.CheckSignatureFrom(cert); err != nil {
+			continue
+		}
+		rootIssuers++
+	}
+
+	return totalIssuers, rootIssuers, nil
+}
+
+func isAcmeEnabled(fetcher *PathFetch) (bool, error) {
+	isEnabledRaw, ok := fetcher.Secret.Data["enabled"]
+	if !ok {
+		return false, fmt.Errorf("enabled configuration field missing from acme config")
+	}
+
+	parseBool, err := parseutil.ParseBool(isEnabledRaw)
+	if err != nil {
+		return false, fmt.Errorf("failed parsing 'enabled' field from ACME config: %w", err)
+	}
+
+	return parseBool, nil
+}
+
+func verifyLocalPathUrl(h *EnableAcmeIssuance) error {
+	localPathRaw, ok := h.ClusterConfigFetcher.Secret.Data["path"]
+	if !ok {
+		return fmt.Errorf("'path' field missing from config")
+	}
+
+	localPath, err := parseutil.ParseString(localPathRaw)
+	if err != nil {
+		return fmt.Errorf("failed converting 'path' field from local config: %w", err)
+	}
+
+	if localPath == "" {
+		return fmt.Errorf("'path' field not configured within /{{mount}}/config/cluster")
+	}
+
+	parsedUrl, err := url.Parse(localPath)
+	if err != nil {
+		return fmt.Errorf("failed to parse URL from path config: %v: %w", localPathRaw, err)
+	}
+
+	if parsedUrl.Scheme != "https" {
+		return fmt.Errorf("the configured 'path' field in /{{mount}}/config/cluster was not using an https scheme")
+	}
+
+	// Avoid issues with SSL certificates for this check, we just want to validate that we would
+	// hit an ACME server with the path they specified in configuration
+	tr := &http.Transport{
+		TLSClientConfig: &tls.Config{InsecureSkipVerify: true},
+	}
+	client := &http.Client{Transport: tr}
+	acmeDirectoryUrl := parsedUrl.JoinPath("/acme/", "directory")
+	acmeClient := acme.Client{HTTPClient: client, DirectoryURL: acmeDirectoryUrl.String()}
+	_, err = acmeClient.Discover(context.Background())
+	if err != nil {
+		return fmt.Errorf("using configured 'path' field ('%s') in /{{mount}}/config/cluster failed to reach the ACME"+
+			" directory: %s: %w", parsedUrl.String(), acmeDirectoryUrl.String(), err)
+	}
+
+	return nil
+}
+
+func (h *EnableAcmeIssuance) Evaluate(e *Executor) (results []*Result, err error) {
+	if h.UnsupportedVersion {
+		ret := Result{
+			Status:   ResultInvalidVersion,
+			Endpoint: h.AcmeConfigFetcher.Path,
+			Message:  "This health check requires Vault 1.14+ but an earlier version of Vault Server was contacted, preventing this health check from running.",
+		}
+		return []*Result{&ret}, nil
+	}
+
+	if h.AcmeConfigFetcher.IsSecretPermissionsError() {
+		msg := "Without this information, this health check is unable to function."
+		return craftInsufficientPermissionResult(e, h.AcmeConfigFetcher.Path, msg), nil
+	}
+
+	acmeEnabled, err := isAcmeEnabled(h.AcmeConfigFetcher)
+	if err != nil {
+		return nil, err
+	}
+
+	if !acmeEnabled {
+		if h.TotalIssuers == 0 {
+			ret := Result{
+				Status:   ResultNotApplicable,
+				Endpoint: h.AcmeConfigFetcher.Path,
+				Message:  "No issuers in mount, ACME is not required.",
+			}
+			return []*Result{&ret}, nil
+		}
+
+		if h.TotalIssuers == h.RootIssuers {
+			ret := Result{
+				Status:   ResultNotApplicable,
+				Endpoint: h.AcmeConfigFetcher.Path,
+				Message:  "Mount contains only root issuers, ACME is not required.",
+			}
+			return []*Result{&ret}, nil
+		}
+
+		ret := Result{
+			Status:   ResultInformational,
+			Endpoint: h.AcmeConfigFetcher.Path,
+			Message:  "Consider enabling ACME support to support a self-rotating PKI infrastructure.",
+		}
+		return []*Result{&ret}, nil
+	}
+
+	if h.ClusterConfigFetcher.IsSecretPermissionsError() {
+		msg := "Without this information, this health check is unable to function."
+		return craftInsufficientPermissionResult(e, h.ClusterConfigFetcher.Path, msg), nil
+	}
+
+	localPathIssue := verifyLocalPathUrl(h)
+
+	if localPathIssue != nil {
+		ret := Result{
+			Status:   ResultWarning,
+			Endpoint: h.ClusterConfigFetcher.Path,
+			Message:  "ACME enabled in config but not functional: " + localPathIssue.Error(),
+		}
+		return []*Result{&ret}, nil
+	}
+
+	ret := Result{
+		Status:   ResultOK,
+		Endpoint: h.ClusterConfigFetcher.Path,
+		Message:  "ACME enabled and successfully connected to the ACME directory.",
+	}
+	return []*Result{&ret}, nil
+}
diff --git a/command/pki_health_check.go b/command/pki_health_check.go
index c44245ccd..188c95c99 100644
--- a/command/pki_health_check.go
+++ b/command/pki_health_check.go
@@ -220,6 +220,8 @@ func (c *PKIHealthCheckCommand) Run(args []string) int {
 	executor.AddCheck(healthcheck.NewEnableAutoTidyCheck())
 	executor.AddCheck(healthcheck.NewTidyLastRunCheck())
 	executor.AddCheck(healthcheck.NewTooManyCertsCheck())
+	executor.AddCheck(healthcheck.NewEnableAcmeIssuance())
+	executor.AddCheck(healthcheck.NewAllowAcmeHeaders())
 	if c.flagDefaultDisabled {
 		executor.DefaultEnabled = false
 	}
diff --git a/command/pki_health_check_test.go b/command/pki_health_check_test.go
index d44f789f5..93d231593 100644
--- a/command/pki_health_check_test.go
+++ b/command/pki_health_check_test.go
@@ -7,6 +7,7 @@ import (
 	"bytes"
 	"encoding/json"
 	"fmt"
+	"net/url"
 	"strings"
 	"testing"
 	"time"
@@ -30,7 +31,7 @@ func TestPKIHC_AllGood(t *testing.T) {
 			AuditNonHMACRequestKeys:   healthcheck.VisibleReqParams,
 			AuditNonHMACResponseKeys:  healthcheck.VisibleRespParams,
 			PassthroughRequestHeaders: []string{"If-Modified-Since"},
-			AllowedResponseHeaders:    []string{"Last-Modified"},
+			AllowedResponseHeaders:    []string{"Last-Modified", "Replay-Nonce", "Link", "Location"},
 			MaxLeaseTTL:               "36500d",
 		},
 	}); err != nil {
@@ -69,6 +70,21 @@ func TestPKIHC_AllGood(t *testing.T) {
 		t.Fatalf("failed to run tidy: %v", err)
 	}
 
+	path, err := url.Parse(client.Address())
+	require.NoError(t, err, "failed parsing client address")
+
+	if _, err := client.Logical().Write("pki/config/cluster", map[string]interface{}{
+		"path": path.JoinPath("/v1/", "pki/").String(),
+	}); err != nil {
+		t.Fatalf("failed to update local cluster: %v", err)
+	}
+
+	if _, err := client.Logical().Write("pki/config/acme", map[string]interface{}{
+		"enabled": "true",
+	}); err != nil {
+		t.Fatalf("failed to update acme config: %v", err)
+	}
+
 	_, _, results := execPKIHC(t, client, true)
 
 	validateExpectedPKIHC(t, expectedAllGood, results)
@@ -345,6 +361,11 @@ var expectedAllGood = map[string][]map[string]interface{}{
 			"status": "ok",
 		},
 	},
+	"allow_acme_headers": {
+		{
+			"status": "ok",
+		},
+	},
 	"allow_if_modified_since": {
 		{
 			"status": "ok",
@@ -355,6 +376,11 @@ var expectedAllGood = map[string][]map[string]interface{}{
 			"status": "ok",
 		},
 	},
+	"enable_acme_issuance": {
+		{
+			"status": "ok",
+		},
+	},
 	"enable_auto_tidy": {
 		{
 			"status": "ok",
@@ -406,6 +432,11 @@ var expectedAllBad = map[string][]map[string]interface{}{
 			"status": "critical",
 		},
 	},
+	"allow_acme_headers": {
+		{
+			"status": "not_applicable",
+		},
+	},
 	"allow_if_modified_since": {
 		{
 			"status": "informational",
@@ -503,6 +534,11 @@ var expectedAllBad = map[string][]map[string]interface{}{
 			"status": "informational",
 		},
 	},
+	"enable_acme_issuance": {
+		{
+			"status": "not_applicable",
+		},
+	},
 	"enable_auto_tidy": {
 		{
 			"status": "informational",
@@ -554,8 +590,18 @@ var expectedEmptyWithIssuer = map[string][]map[string]interface{}{
 			"status": "ok",
 		},
 	},
+	"allow_acme_headers": {
+		{
+			"status": "not_applicable",
+		},
+	},
 	"allow_if_modified_since": nil,
 	"audit_visibility":        nil,
+	"enable_acme_issuance": {
+		{
+			"status": "not_applicable",
+		},
+	},
 	"enable_auto_tidy": {
 		{
 			"status": "informational",
@@ -598,8 +644,18 @@ var expectedNoPerm = map[string][]map[string]interface{}{
 			"status": "critical",
 		},
 	},
+	"allow_acme_headers": {
+		{
+			"status": "insufficient_permissions",
+		},
+	},
 	"allow_if_modified_since": nil,
 	"audit_visibility":        nil,
+	"enable_acme_issuance": {
+		{
+			"status": "insufficient_permissions",
+		},
+	},
 	"enable_auto_tidy": {
 		{
 			"status": "insufficient_permissions",