diff --git a/cmd/acmesolver/main.go b/cmd/acmesolver/main.go
index e776c50f9..3cc075dbf 100644
--- a/cmd/acmesolver/main.go
+++ b/cmd/acmesolver/main.go
@@ -39,8 +39,8 @@ var (
 func main() {
 	logs.InitLogs(nil)
 	defer logs.FlushLogs()
-
 	flag.Parse()
+	ctx := logs.NewContext(nil, nil, "acmesolver")
 
 	s := &solver.HTTP01Solver{
 		ListenPort: *listenPort,
@@ -49,7 +49,7 @@ func main() {
 		Key:        *key,
 	}
 
-	if err := s.Listen(); err != nil {
+	if err := s.Listen(ctx); err != nil {
 		log.Fatalf("error listening for connections: %s", err.Error())
 	}
 }
diff --git a/pkg/issuer/acme/http/solver/BUILD.bazel b/pkg/issuer/acme/http/solver/BUILD.bazel
index b24fcdfd4..1c486b17e 100644
--- a/pkg/issuer/acme/http/solver/BUILD.bazel
+++ b/pkg/issuer/acme/http/solver/BUILD.bazel
@@ -8,6 +8,7 @@ go_library(
     ],
     importpath = "github.com/jetstack/cert-manager/pkg/issuer/acme/http/solver",
     visibility = ["//visibility:public"],
+    deps = ["//pkg/logs:go_default_library"],
 )
 
 filegroup(
diff --git a/pkg/issuer/acme/http/solver/solver.go b/pkg/issuer/acme/http/solver/solver.go
index cd91128fc..bc7edd22e 100644
--- a/pkg/issuer/acme/http/solver/solver.go
+++ b/pkg/issuer/acme/http/solver/solver.go
@@ -17,11 +17,13 @@ limitations under the License.
 package solver
 
 import (
+	"context"
 	"fmt"
-	"log"
 	"net/http"
 	"path"
 	"strings"
+
+	logf "github.com/jetstack/cert-manager/pkg/logs"
 )
 
 type HTTP01Solver struct {
@@ -32,43 +34,56 @@ type HTTP01Solver struct {
 	Key    string
 }
 
-func (h *HTTP01Solver) Listen() error {
+func (h *HTTP01Solver) Listen(ctx context.Context) error {
+	log := logf.FromContext(ctx)
+	log.Info("starting listener",
+		"expected_domain", h.Domain,
+		"expected_token", h.Token,
+		"expected_key", h.Key,
+		"listen_port", h.ListenPort,
+	)
+
 	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		// extract vars from the request
 		host := strings.Split(r.Host, ":")[0]
 		basePath := path.Dir(r.URL.EscapedPath())
 		token := path.Base(r.URL.EscapedPath())
 
+		log := log.WithValues(
+			"host", host,
+			"path", r.URL.EscapedPath(),
+			"base_path", basePath,
+			"token", token,
+		)
 		if r.URL.EscapedPath() == "/" || r.URL.EscapedPath() == "/healthz" {
-			log.Printf("[%s] Responding OK to health check '%s'", h.Domain, r.URL.EscapedPath())
+			log.Info("responding OK to health check")
 			w.WriteHeader(http.StatusOK)
 			return
 		}
-
-		log.Printf("[%s] Validating request. basePath=%s, token=%s", h.Domain, basePath, token)
+		log.Info("validating request")
 		// verify the base path is correct
 		if basePath != HTTPChallengePath {
-			log.Printf("[%s] Invalid basePath, got '%s' but expected '%s'", h.Domain, basePath, HTTPChallengePath)
+			log.Info("invalid base_path", "expected_base_path", HTTPChallengePath)
 			http.NotFound(w, r)
 			return
 		}
 
-		log.Printf("[%s] Comparing actual host '%s' against expected '%s'", host, host, h.Domain)
-
+		log.Info("comparing host", "expected_host", h.Domain)
 		if h.Domain != host {
-			log.Printf("[%s] Invalid host '%s'", h.Domain, host)
+			log.Info("invalid host", "expected_host", h.Domain)
 			http.NotFound(w, r)
 			return
 		}
 
+		log.Info("comparing token", "expected_token", h.Token)
 		if h.Token != token {
 			// if nothing else, we return a 404 here
-			log.Printf("[%s] Invalid token '%s', expected: '%s'", h.Domain, token, h.Token)
+			log.Info("invalid token", "expected_token", h.Token)
 			http.NotFound(w, r)
 			return
 		}
 
-		log.Printf("[%s] Got successful challenge request, writing key...", h.Domain)
+		log.Info("got successful challenge request, writing key")
 		w.WriteHeader(http.StatusOK)
 		fmt.Fprint(w, h.Key)
 	})