diff --git a/acme/http.go b/acme/http.go
index 180db786..dc958046 100644
--- a/acme/http.go
+++ b/acme/http.go
@@ -31,14 +31,14 @@ const (
 func httpHead(url string) (resp *http.Response, err error) {
 	req, err := http.NewRequest("HEAD", url, nil)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("failed to head %q: %v", url, err)
 	}
 
 	req.Header.Set("User-Agent", userAgent())
 
 	resp, err = HTTPClient.Do(req)
 	if err != nil {
-		return resp, err
+		return resp, fmt.Errorf("failed to do head %q: %v", url, err)
 	}
 	resp.Body.Close()
 	return resp, err
@@ -49,7 +49,7 @@ func httpHead(url string) (resp *http.Response, err error) {
 func httpPost(url string, bodyType string, body io.Reader) (resp *http.Response, err error) {
 	req, err := http.NewRequest("POST", url, body)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("failed to post %q: %v", url, err)
 	}
 	req.Header.Set("Content-Type", bodyType)
 	req.Header.Set("User-Agent", userAgent())
@@ -62,7 +62,7 @@ func httpPost(url string, bodyType string, body io.Reader) (resp *http.Response,
 func httpGet(url string) (resp *http.Response, err error) {
 	req, err := http.NewRequest("GET", url, nil)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("failed to get %q: %v", url, err)
 	}
 	req.Header.Set("User-Agent", userAgent())
 
@@ -74,7 +74,7 @@ func httpGet(url string) (resp *http.Response, err error) {
 func getJSON(uri string, respBody interface{}) (http.Header, error) {
 	resp, err := httpGet(uri)
 	if err != nil {
-		return nil, fmt.Errorf("failed to get %q: %v", uri, err)
+		return nil, fmt.Errorf("failed to get json %q: %v", uri, err)
 	}
 	defer resp.Body.Close()
 
diff --git a/acme/jws.go b/acme/jws.go
index 876b39b7..1b4d29d5 100644
--- a/acme/jws.go
+++ b/acme/jws.go
@@ -37,7 +37,7 @@ func keyAsJWK(key interface{}) *jose.JsonWebKey {
 func (j *jws) post(url string, content []byte) (*http.Response, error) {
 	signedContent, err := j.signContent(content)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("Failed to sign content -> %s", err.Error())
 	}
 
 	resp, err := httpPost(url, "application/jose+json", bytes.NewBuffer([]byte(signedContent.FullSerialize())))
@@ -54,14 +54,14 @@ func (j *jws) post(url string, content []byte) (*http.Response, error) {
 			// In case of a nonce error - retry once
 			resp, err = httpPost(url, "application/jose+json", bytes.NewBuffer([]byte(signedContent.FullSerialize())))
 			if err != nil {
-				return nil, err
+				return nil, fmt.Errorf("Failed to HTTP POST to %s -> %s", url, err.Error())
 			}
 		default:
-			return nil, err
+			return nil, fmt.Errorf("Failed to HTTP POST to %s -> %s", url, err.Error())
 		}
 	}
 
-	return resp, err
+	return resp, nil
 }
 
 func (j *jws) signContent(content []byte) (*jose.JsonWebSignature, error) {
@@ -80,13 +80,13 @@ func (j *jws) signContent(content []byte) (*jose.JsonWebSignature, error) {
 
 	signer, err := jose.NewSigner(alg, j.privKey)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("Failed to create jose signer -> %s", err.Error())
 	}
 	signer.SetNonceSource(j)
 
 	signed, err := signer.Sign(content)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("Failed to sign content -> %s", err.Error())
 	}
 	return signed, nil
 }
@@ -126,7 +126,7 @@ func (n *nonceManager) Push(nonce string) {
 func getNonce(url string) (string, error) {
 	resp, err := httpHead(url)
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("Failed to get nonce from HTTP HEAD -> %s", err.Error())
 	}
 
 	return getNonceFromResponse(resp)