diff --git a/coderd/coderd.go b/coderd/coderd.go
index d30035bcb6..2a6078bf27 100644
--- a/coderd/coderd.go
+++ b/coderd/coderd.go
@@ -25,7 +25,6 @@ import (
 	"github.com/prometheus/client_golang/prometheus"
 	httpSwagger "github.com/swaggo/http-swagger/v2"
 	"go.opentelemetry.io/otel/trace"
-	"golang.org/x/exp/slices"
 	"golang.org/x/xerrors"
 	"google.golang.org/api/idtoken"
 	"storj.io/drpc/drpcmux"
@@ -408,30 +407,26 @@ func New(options *Options) *API {
 
 	if options.HealthcheckFunc == nil {
 		options.HealthcheckFunc = func(ctx context.Context, apiKey string) *healthcheck.Report {
-			dismissedHealthchecks := loadDismissedHealthchecks(ctx, options.Database, options.Logger)
+			// NOTE: dismissed healthchecks are marked in formatHealthcheck.
+			// Not here, as this result gets cached.
 			return healthcheck.Run(ctx, &healthcheck.ReportOptions{
 				Database: healthcheck.DatabaseReportOptions{
 					DB:        options.Database,
 					Threshold: options.DeploymentValues.Healthcheck.ThresholdDatabase.Value(),
-					Dismissed: slices.Contains(dismissedHealthchecks, codersdk.HealthSectionDatabase),
 				},
 				Websocket: healthcheck.WebsocketReportOptions{
 					AccessURL: options.AccessURL,
 					APIKey:    apiKey,
-					Dismissed: slices.Contains(dismissedHealthchecks, codersdk.HealthSectionWebsocket),
 				},
 				AccessURL: healthcheck.AccessURLReportOptions{
 					AccessURL: options.AccessURL,
-					Dismissed: slices.Contains(dismissedHealthchecks, codersdk.HealthSectionAccessURL),
 				},
 				DerpHealth: derphealth.ReportOptions{
-					DERPMap:   api.DERPMap(),
-					Dismissed: slices.Contains(dismissedHealthchecks, codersdk.HealthSectionDERP),
+					DERPMap: api.DERPMap(),
 				},
 				WorkspaceProxy: healthcheck.WorkspaceProxyReportOptions{
 					CurrentVersion:               buildinfo.Version(),
 					WorkspaceProxiesFetchUpdater: *(options.WorkspaceProxiesFetchUpdater).Load(),
-					Dismissed:                    slices.Contains(dismissedHealthchecks, codersdk.HealthSectionWorkspaceProxy),
 				},
 			})
 		}
diff --git a/coderd/debug.go b/coderd/debug.go
index 16ffb8e179..0e9bb6acbb 100644
--- a/coderd/debug.go
+++ b/coderd/debug.go
@@ -59,6 +59,11 @@ func (api *API) debugDeploymentHealth(rw http.ResponseWriter, r *http.Request) {
 	ctx, cancel := context.WithTimeout(r.Context(), api.Options.HealthcheckTimeout)
 	defer cancel()
 
+	// Load sections previously marked as dismissed.
+	// We hydrate this here as we cache the healthcheck and hydrating in the
+	// healthcheck function itself can lead to stale results.
+	dismissed := loadDismissedHealthchecks(ctx, api.Database, api.Logger)
+
 	// Check if the forced query parameter is set.
 	forced := r.URL.Query().Get("force") == "true"
 
@@ -66,7 +71,7 @@ func (api *API) debugDeploymentHealth(rw http.ResponseWriter, r *http.Request) {
 	if !forced {
 		if report := api.healthCheckCache.Load(); report != nil {
 			if time.Since(report.Time) < api.Options.HealthcheckRefresh {
-				formatHealthcheck(ctx, rw, r, report)
+				formatHealthcheck(ctx, rw, r, *report, dismissed...)
 				return
 			}
 		}
@@ -89,12 +94,36 @@ func (api *API) debugDeploymentHealth(rw http.ResponseWriter, r *http.Request) {
 		})
 		return
 	case res := <-resChan:
-		formatHealthcheck(ctx, rw, r, res.Val)
+		report := res.Val
+		if report == nil {
+			httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+				Message: "There was an unknown error completing the healthcheck.",
+				Detail:  "nil report from healthcheck result channel",
+			})
+			return
+		}
+		formatHealthcheck(ctx, rw, r, *report, dismissed...)
 		return
 	}
 }
 
-func formatHealthcheck(ctx context.Context, rw http.ResponseWriter, r *http.Request, hc *healthcheck.Report) {
+func formatHealthcheck(ctx context.Context, rw http.ResponseWriter, r *http.Request, hc healthcheck.Report, dismissed ...codersdk.HealthSection) {
+	// Mark any sections previously marked as dismissed.
+	for _, d := range dismissed {
+		switch d {
+		case codersdk.HealthSectionAccessURL:
+			hc.AccessURL.Dismissed = true
+		case codersdk.HealthSectionDERP:
+			hc.DERP.Dismissed = true
+		case codersdk.HealthSectionDatabase:
+			hc.Database.Dismissed = true
+		case codersdk.HealthSectionWebsocket:
+			hc.Websocket.Dismissed = true
+		case codersdk.HealthSectionWorkspaceProxy:
+			hc.WorkspaceProxy.Dismissed = true
+		}
+	}
+
 	format := r.URL.Query().Get("format")
 	switch format {
 	case "text":
@@ -269,7 +298,7 @@ func loadDismissedHealthchecks(ctx context.Context, db database.Store, logger sl
 		}
 	}
 	if err != nil && !xerrors.Is(err, sql.ErrNoRows) {
-		logger.Error(ctx, "unable to fetch health settings: %w", err)
+		logger.Error(ctx, "unable to fetch health settings", slog.Error(err))
 	}
 	return dismissedHealthchecks
 }
diff --git a/coderd/debug_test.go b/coderd/debug_test.go
index 7a020eac67..faa8efe747 100644
--- a/coderd/debug_test.go
+++ b/coderd/debug_test.go
@@ -2,6 +2,7 @@ package coderd_test
 
 import (
 	"context"
+	"encoding/json"
 	"io"
 	"net/http"
 	"sync/atomic"
@@ -11,6 +12,8 @@ import (
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 
+	"cdr.dev/slog/sloggers/slogtest"
+
 	"github.com/coder/coder/v2/coderd/coderdtest"
 	"github.com/coder/coder/v2/coderd/healthcheck"
 	"github.com/coder/coder/v2/coderd/healthcheck/derphealth"
@@ -90,8 +93,11 @@ func TestDebugHealth(t *testing.T) {
 		t.Parallel()
 
 		var (
+			// Need to ignore errors due to ctx timeout
+			logger      = slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
 			ctx, cancel = context.WithTimeout(context.Background(), testutil.WaitShort)
 			client      = coderdtest.New(t, &coderdtest.Options{
+				Logger:             &logger,
 				HealthcheckTimeout: time.Microsecond,
 				HealthcheckFunc: func(context.Context, string) *healthcheck.Report {
 					t := time.NewTimer(time.Second)
@@ -276,6 +282,17 @@ func TestHealthSettings(t *testing.T) {
 		settings, err := adminClient.HealthSettings(ctx)
 		require.NoError(t, err)
 		require.Equal(t, expected, settings)
+
+		// then
+		res, err := adminClient.Request(ctx, "GET", "/api/v2/debug/health", nil)
+		require.NoError(t, err)
+		bs, err := io.ReadAll(res.Body)
+		require.NoError(t, err)
+		defer res.Body.Close()
+		var hc healthcheck.Report
+		require.NoError(t, json.Unmarshal(bs, &hc))
+		require.True(t, hc.DERP.Dismissed)
+		require.True(t, hc.Websocket.Dismissed)
 	})
 
 	t.Run("UnDismissSection", func(t *testing.T) {
@@ -307,6 +324,17 @@ func TestHealthSettings(t *testing.T) {
 		settings, err := adminClient.HealthSettings(ctx)
 		require.NoError(t, err)
 		require.Equal(t, expected, settings)
+
+		// then
+		res, err := adminClient.Request(ctx, "GET", "/api/v2/debug/health", nil)
+		require.NoError(t, err)
+		bs, err := io.ReadAll(res.Body)
+		require.NoError(t, err)
+		defer res.Body.Close()
+		var hc healthcheck.Report
+		require.NoError(t, json.Unmarshal(bs, &hc))
+		require.True(t, hc.DERP.Dismissed)
+		require.False(t, hc.Websocket.Dismissed)
 	})
 
 	t.Run("NotModified", func(t *testing.T) {