diff --git a/health/api/api_test.go b/health/api/api_test.go
index 66aa6b419..f93d696f3 100644
--- a/health/api/api_test.go
+++ b/health/api/api_test.go
@@ -1,6 +1,7 @@
 package api
 
 import (
+	"context"
 	"net/http"
 	"net/http/httptest"
 	"testing"
@@ -59,7 +60,7 @@ func TestPOSTDownHandlerChangeStatus(t *testing.T) {
 		t.Errorf("Did not get a 200.")
 	}
 
-	if len(health.CheckStatus()) != 1 {
+	if len(health.CheckStatus(context.Background())) != 1 {
 		t.Errorf("DownHandler didn't add an error check.")
 	}
 }
@@ -80,7 +81,7 @@ func TestPOSTUpHandlerChangeStatus(t *testing.T) {
 		t.Errorf("Did not get a 200.")
 	}
 
-	if len(health.CheckStatus()) != 0 {
+	if len(health.CheckStatus(context.Background())) != 0 {
 		t.Errorf("UpHandler didn't remove the error check.")
 	}
 }
diff --git a/health/checks/checks.go b/health/checks/checks.go
index 846ca2015..9382db32e 100644
--- a/health/checks/checks.go
+++ b/health/checks/checks.go
@@ -1,13 +1,13 @@
 package checks
 
 import (
+	"context"
 	"errors"
 	"fmt"
 	"net"
 	"net/http"
 	"os"
 	"path/filepath"
-	"strconv"
 	"time"
 
 	"github.com/distribution/distribution/v3/health"
@@ -16,7 +16,7 @@ import (
 // FileChecker checks the existence of a file and returns an error
 // if the file exists.
 func FileChecker(f string) health.Checker {
-	return health.CheckFunc(func() error {
+	return health.CheckFunc(func(context.Context) error {
 		absoluteFilePath, err := filepath.Abs(f)
 		if err != nil {
 			return fmt.Errorf("failed to get absolute path for %q: %v", f, err)
@@ -36,13 +36,13 @@ func FileChecker(f string) health.Checker {
 // HTTPChecker does a HEAD request and verifies that the HTTP status code
 // returned matches statusCode.
 func HTTPChecker(r string, statusCode int, timeout time.Duration, headers http.Header) health.Checker {
-	return health.CheckFunc(func() error {
+	return health.CheckFunc(func(ctx context.Context) error {
 		client := http.Client{
 			Timeout: timeout,
 		}
-		req, err := http.NewRequest(http.MethodHead, r, nil)
+		req, err := http.NewRequestWithContext(ctx, http.MethodHead, r, nil)
 		if err != nil {
-			return errors.New("error creating request: " + r)
+			return fmt.Errorf("%v: error creating request: %w", r, err)
 		}
 		for headerName, headerValues := range headers {
 			for _, headerValue := range headerValues {
@@ -51,11 +51,11 @@ func HTTPChecker(r string, statusCode int, timeout time.Duration, headers http.H
 		}
 		response, err := client.Do(req)
 		if err != nil {
-			return errors.New("error while checking: " + r)
+			return fmt.Errorf("%v: error while checking: %w", r, err)
 		}
 		defer response.Body.Close()
 		if response.StatusCode != statusCode {
-			return errors.New("downstream service returned unexpected status: " + strconv.Itoa(response.StatusCode))
+			return fmt.Errorf("%v: downstream service returned unexpected status: %d", r, response.StatusCode)
 		}
 		return nil
 	})
@@ -63,10 +63,11 @@ func HTTPChecker(r string, statusCode int, timeout time.Duration, headers http.H
 
 // TCPChecker attempts to open a TCP connection.
 func TCPChecker(addr string, timeout time.Duration) health.Checker {
-	return health.CheckFunc(func() error {
-		conn, err := net.DialTimeout("tcp", addr, timeout)
+	return health.CheckFunc(func(ctx context.Context) error {
+		d := net.Dialer{Timeout: timeout}
+		conn, err := d.DialContext(ctx, "tcp", addr)
 		if err != nil {
-			return errors.New("connection to " + addr + " failed")
+			return fmt.Errorf("%v: connection failed: %w", addr, err)
 		}
 		conn.Close()
 		return nil
diff --git a/health/checks/checks_test.go b/health/checks/checks_test.go
index 6b6dd14fa..60332f180 100644
--- a/health/checks/checks_test.go
+++ b/health/checks/checks_test.go
@@ -1,25 +1,26 @@
 package checks
 
 import (
+	"context"
 	"testing"
 )
 
 func TestFileChecker(t *testing.T) {
-	if err := FileChecker("/tmp").Check(); err == nil {
+	if err := FileChecker("/tmp").Check(context.Background()); err == nil {
 		t.Errorf("/tmp was expected as exists")
 	}
 
-	if err := FileChecker("NoSuchFileFromMoon").Check(); err != nil {
+	if err := FileChecker("NoSuchFileFromMoon").Check(context.Background()); err != nil {
 		t.Errorf("NoSuchFileFromMoon was expected as not exists, error:%v", err)
 	}
 }
 
 func TestHTTPChecker(t *testing.T) {
-	if err := HTTPChecker("https://www.google.cybertron", 200, 0, nil).Check(); err == nil {
+	if err := HTTPChecker("https://www.google.cybertron", 200, 0, nil).Check(context.Background()); err == nil {
 		t.Errorf("Google on Cybertron was expected as not exists")
 	}
 
-	if err := HTTPChecker("https://www.google.pt", 200, 0, nil).Check(); err != nil {
+	if err := HTTPChecker("https://www.google.pt", 200, 0, nil).Check(context.Background()); err != nil {
 		t.Errorf("Google at Portugal was expected as exists, error:%v", err)
 	}
 }
diff --git a/health/health.go b/health/health.go
index 67873f597..89cd7c4f3 100644
--- a/health/health.go
+++ b/health/health.go
@@ -1,6 +1,7 @@
 package health
 
 import (
+	"context"
 	"encoding/json"
 	"fmt"
 	"net/http"
@@ -35,17 +36,17 @@ var DefaultRegistry *Registry
 // Checker is the interface for a Health Checker
 type Checker interface {
 	// Check returns nil if the service is okay.
-	Check() error
+	Check(context.Context) error
 }
 
 // CheckFunc is a convenience type to create functions that implement
 // the Checker interface
-type CheckFunc func() error
+type CheckFunc func(context.Context) error
 
 // Check Implements the Checker interface to allow for any func() error method
 // to be passed as a Checker
-func (cf CheckFunc) Check() error {
-	return cf()
+func (cf CheckFunc) Check(ctx context.Context) error {
+	return cf(ctx)
 }
 
 // Updater implements a health check that is explicitly set.
@@ -66,7 +67,7 @@ type updater struct {
 }
 
 // Check implements the Checker interface
-func (u *updater) Check() error {
+func (u *updater) Check(context.Context) error {
 	u.mu.Lock()
 	defer u.mu.Unlock()
 
@@ -99,7 +100,7 @@ type thresholdUpdater struct {
 }
 
 // Check implements the Checker interface
-func (tu *thresholdUpdater) Check() error {
+func (tu *thresholdUpdater) Check(context.Context) error {
 	tu.mu.Lock()
 	defer tu.mu.Unlock()
 
@@ -138,7 +139,7 @@ func PeriodicChecker(check Checker, period time.Duration) Checker {
 		defer t.Stop()
 		for {
 			<-t.C
-			u.Update(check.Check())
+			u.Update(check.Check(context.Background()))
 		}
 	}()
 
@@ -154,7 +155,7 @@ func PeriodicThresholdChecker(check Checker, period time.Duration, threshold int
 		defer t.Stop()
 		for {
 			<-t.C
-			tu.Update(check.Check())
+			tu.Update(check.Check(context.Background()))
 		}
 	}()
 
@@ -162,12 +163,12 @@ func PeriodicThresholdChecker(check Checker, period time.Duration, threshold int
 }
 
 // CheckStatus returns a map with all the current health check errors
-func (registry *Registry) CheckStatus() map[string]string { // TODO(stevvooe) this needs a proper type
+func (registry *Registry) CheckStatus(ctx context.Context) map[string]string { // TODO(stevvooe) this needs a proper type
 	registry.mu.RLock()
 	defer registry.mu.RUnlock()
 	statusKeys := make(map[string]string)
 	for k, v := range registry.registeredChecks {
-		err := v.Check()
+		err := v.Check(ctx)
 		if err != nil {
 			statusKeys[k] = err.Error()
 		}
@@ -178,8 +179,8 @@ func (registry *Registry) CheckStatus() map[string]string { // TODO(stevvooe) th
 
 // CheckStatus returns a map with all the current health check errors from the
 // default registry.
-func CheckStatus() map[string]string {
-	return DefaultRegistry.CheckStatus()
+func CheckStatus(ctx context.Context) map[string]string {
+	return DefaultRegistry.CheckStatus(ctx)
 }
 
 // Register associates the checker with the provided name.
@@ -203,19 +204,19 @@ func Register(name string, check Checker) {
 }
 
 // RegisterFunc allows the convenience of registering a checker directly from
-// an arbitrary func() error.
-func (registry *Registry) RegisterFunc(name string, check func() error) {
-	registry.Register(name, CheckFunc(check))
+// an arbitrary func(context.Context) error.
+func (registry *Registry) RegisterFunc(name string, check CheckFunc) {
+	registry.Register(name, check)
 }
 
 // RegisterFunc allows the convenience of registering a checker in the default
-// registry directly from an arbitrary func() error.
-func RegisterFunc(name string, check func() error) {
+// registry directly from an arbitrary func(context.Context) error.
+func RegisterFunc(name string, check CheckFunc) {
 	DefaultRegistry.RegisterFunc(name, check)
 }
 
 // RegisterPeriodicFunc allows the convenience of registering a PeriodicChecker
-// from an arbitrary func() error.
+// from an arbitrary func(context.Context) error.
 func (registry *Registry) RegisterPeriodicFunc(name string, period time.Duration, check CheckFunc) {
 	registry.Register(name, PeriodicChecker(check, period))
 }
@@ -243,7 +244,7 @@ func RegisterPeriodicThresholdFunc(name string, period time.Duration, threshold
 // Returns 503 if any Error status exists, 200 otherwise
 func StatusHandler(w http.ResponseWriter, r *http.Request) {
 	if r.Method == http.MethodGet {
-		checks := CheckStatus()
+		checks := CheckStatus(r.Context())
 		status := http.StatusOK
 
 		// If there is an error, return 503
@@ -263,7 +264,7 @@ func StatusHandler(w http.ResponseWriter, r *http.Request) {
 // disable a web application when the health checks fail.
 func Handler(handler http.Handler) http.Handler {
 	return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
-		checks := CheckStatus()
+		checks := CheckStatus(r.Context())
 		if len(checks) != 0 {
 			// NOTE(milosgajdos): disable errcheck as the error is
 			// accessible via /debug/health
diff --git a/health/health_test.go b/health/health_test.go
index 80b5ebed6..c877ed7fe 100644
--- a/health/health_test.go
+++ b/health/health_test.go
@@ -1,6 +1,7 @@
 package health
 
 import (
+	"context"
 	"errors"
 	"fmt"
 	"net/http"
@@ -36,7 +37,7 @@ func TestReturns503IfThereAreErrorChecks(t *testing.T) {
 	}
 
 	// Create a manual error
-	Register("some_check", CheckFunc(func() error {
+	Register("some_check", CheckFunc(func(context.Context) error {
 		return errors.New("This Check did not succeed")
 	}))
 
diff --git a/registry/handlers/app.go b/registry/handlers/app.go
index fb8e9dd29..0e4d528b8 100644
--- a/registry/handlers/app.go
+++ b/registry/handlers/app.go
@@ -348,7 +348,7 @@ func (app *App) RegisterHealthChecks(healthRegistries ...*health.Registry) {
 			interval = defaultCheckInterval
 		}
 
-		storageDriverCheck := func() error {
+		storageDriverCheck := func(context.Context) error {
 			_, err := app.driver.Stat(app, "/") // "/" should always exist
 			if _, ok := err.(storagedriver.PathNotFoundError); ok {
 				err = nil // pass this through, backend is responding, but this path doesn't exist.
diff --git a/registry/handlers/health_test.go b/registry/handlers/health_test.go
index dc706b870..079ebda51 100644
--- a/registry/handlers/health_test.go
+++ b/registry/handlers/health_test.go
@@ -5,6 +5,7 @@ import (
 	"net/http"
 	"net/http/httptest"
 	"os"
+	"strings"
 	"testing"
 	"time"
 
@@ -48,7 +49,7 @@ func TestFileHealthCheck(t *testing.T) {
 	// Wait for health check to happen
 	<-time.After(2 * interval)
 
-	status := healthRegistry.CheckStatus()
+	status := healthRegistry.CheckStatus(ctx)
 	if len(status) != 1 {
 		t.Fatal("expected 1 item in health check results")
 	}
@@ -59,7 +60,7 @@ func TestFileHealthCheck(t *testing.T) {
 	os.Remove(tmpfile.Name())
 
 	<-time.After(2 * interval)
-	if len(healthRegistry.CheckStatus()) != 0 {
+	if len(healthRegistry.CheckStatus(ctx)) != 0 {
 		t.Fatal("expected 0 items in health check results")
 	}
 }
@@ -112,7 +113,7 @@ func TestTCPHealthCheck(t *testing.T) {
 	// Wait for health check to happen
 	<-time.After(2 * interval)
 
-	if len(healthRegistry.CheckStatus()) != 0 {
+	if len(healthRegistry.CheckStatus(ctx)) != 0 {
 		t.Fatal("expected 0 items in health check results")
 	}
 
@@ -120,11 +121,11 @@ func TestTCPHealthCheck(t *testing.T) {
 	<-time.After(2 * interval)
 
 	// Health check should now fail
-	status := healthRegistry.CheckStatus()
+	status := healthRegistry.CheckStatus(ctx)
 	if len(status) != 1 {
 		t.Fatal("expected 1 item in health check results")
 	}
-	if status[addrStr] != "connection to "+addrStr+" failed" {
+	if !strings.Contains(status[addrStr], "connection failed") {
 		t.Fatal(`did not get "connection failed" result for health check`)
 	}
 }
@@ -174,7 +175,7 @@ func TestHTTPHealthCheck(t *testing.T) {
 	for i := 0; ; i++ {
 		<-time.After(interval)
 
-		status := healthRegistry.CheckStatus()
+		status := healthRegistry.CheckStatus(ctx)
 
 		if i < threshold-1 {
 			// definitely shouldn't have hit the threshold yet
@@ -191,7 +192,7 @@ func TestHTTPHealthCheck(t *testing.T) {
 		if len(status) != 1 {
 			t.Fatal("expected 1 item in health check results")
 		}
-		if status[checkedServer.URL] != "downstream service returned unexpected status: 500" {
+		if !strings.Contains(status[checkedServer.URL], "downstream service returned unexpected status: 500") {
 			t.Fatal("did not get expected result for health check")
 		}
 
@@ -203,7 +204,7 @@ func TestHTTPHealthCheck(t *testing.T) {
 
 	<-time.After(2 * interval)
 
-	if len(healthRegistry.CheckStatus()) != 0 {
+	if len(healthRegistry.CheckStatus(ctx)) != 0 {
 		t.Fatal("expected 0 items in health check results")
 	}
 }