diff --git a/caddy/letsencrypt/letsencrypt.go b/caddy/letsencrypt/letsencrypt.go
index 35b24d782..fa19a81fa 100644
--- a/caddy/letsencrypt/letsencrypt.go
+++ b/caddy/letsencrypt/letsencrypt.go
@@ -7,7 +7,6 @@ import (
 	"encoding/json"
 	"errors"
 	"io/ioutil"
-	"log"
 	"net/http"
 	"os"
 	"strings"
@@ -84,11 +83,35 @@ func Activate(configs []server.Config) ([]server.Config, error) {
 		}
 
 		// client is ready, so let's get free, trusted SSL certificates! yeah!
+	Obtain:
 		certificates, failures := obtainCertificates(client, serverConfigs)
 		if len(failures) > 0 {
-			for k, v := range failures {
-				log.Printf("[%s] Failed to get a certificate: %s", k, v)
+			// Build an error string to return, using all the failures in the list.
+			var errMsg string
+
+			// An agreement error means we need to prompt the user (once) with updated terms
+			// while they're still here.
+			var promptedUpdatedTerms bool
+
+			for domain, obtainErr := range failures {
+				// If the failure was simply because the terms have changed, re-prompt and re-try
+				if tosErr, ok := obtainErr.(acme.TOSError); ok && !promptedUpdatedTerms {
+					Agreed = promptUserAgreement(tosErr.Detail, true) // TODO: Use latest URL
+					promptedUpdatedTerms = true
+					if Agreed {
+						err := client.AgreeToTOS()
+						if err != nil {
+							return configs, errors.New("error agreeing to updated terms: " + err.Error())
+						}
+						goto Obtain
+					}
+				}
+
+				// If user did not agree or it was any other kind of error, just append to the list of errors
+				errMsg += "[" + domain + "] failed to get certificate: " + obtainErr.Error() + "\n"
 			}
+
+			return configs, errors.New(errMsg)
 		}
 
 		// ... that's it. save the certs, keys, and metadata files to disk
@@ -213,7 +236,7 @@ func newClient(leEmail string) (*acme.Client, error) {
 		leUser.Registration = reg
 
 		if !Agreed && reg.TosURL == "" {
-			Agreed = promptUserAgreement("<TODO>", false) // TODO
+			Agreed = promptUserAgreement(saURL, false) // TODO - latest URL
 		}
 		if !Agreed && reg.TosURL == "" {
 			return nil, errors.New("user must agree to terms")
diff --git a/caddy/letsencrypt/maintain.go b/caddy/letsencrypt/maintain.go
index ae3647493..7642a238b 100644
--- a/caddy/letsencrypt/maintain.go
+++ b/caddy/letsencrypt/maintain.go
@@ -97,8 +97,8 @@ func renewCertificates(configs []server.Config) (int, []error) {
 		// Directly convert it to days for the following checks.
 		daysLeft := int(expTime.Sub(time.Now().UTC()).Hours() / 24)
 
-		// Renew with a week or less remaining.
-		if daysLeft <= 7 {
+		// Renew with two weeks or less remaining.
+		if daysLeft <= 14 {
 			log.Printf("[INFO] There are %d days left on the certificate of %s. Trying to renew now.", daysLeft, cfg.Host)
 			client, err := newClient("") // email not used for renewal
 			if err != nil {
@@ -127,8 +127,17 @@ func renewCertificates(configs []server.Config) (int, []error) {
 			// Renew certificate.
 			// TODO: revokeOld should be an option in the caddyfile
 			// TODO: bundle should be an option in the caddyfile as well :)
+		Renew:
 			newCertMeta, err := client.RenewCertificate(certMeta, true, true)
 			if err != nil {
+				if _, ok := err.(acme.TOSError); ok {
+					err := client.AgreeToTOS()
+					if err != nil {
+						errs = append(errs, err)
+					}
+					goto Renew
+				}
+
 				time.Sleep(10 * time.Second)
 				newCertMeta, err = client.RenewCertificate(certMeta, true, true)
 				if err != nil {
diff --git a/caddy/letsencrypt/user.go b/caddy/letsencrypt/user.go
index 4d4d48291..7fae3bb41 100644
--- a/caddy/letsencrypt/user.go
+++ b/caddy/letsencrypt/user.go
@@ -146,9 +146,9 @@ func getEmail(cfg server.Config) string {
 		reader := bufio.NewReader(stdin)
 		fmt.Println("Your sites will be served over HTTPS automatically using Let's Encrypt.")
 		fmt.Println("By continuing, you agree to the Let's Encrypt Subscriber Agreement at:")
-		fmt.Println("  https://letsencrypt.org/documents/LE-SA-v1.0.1-July-27-2015.pdf") // TODO: Show current SA link
+		fmt.Println("  " + saURL) // TODO: Show current SA link
 		fmt.Println("Please enter your email address so you can recover your account if needed.")
-		fmt.Println("You can leave it blank, but you lose the ability to recover your account.")
+		fmt.Println("You can leave it blank, but you'll lose the ability to recover your account.")
 		fmt.Print("Email address: ")
 		var err error
 		leEmail, err = reader.ReadString('\n')
@@ -167,10 +167,10 @@ func getEmail(cfg server.Config) string {
 // agreeing, pass false. It returns whether the user agreed or not.
 func promptUserAgreement(agreementURL string, changed bool) bool {
 	if changed {
-		fmt.Printf("The Let's Encrypt Subscriber Agreement has changed:\n%s\n", agreementURL)
+		fmt.Printf("The Let's Encrypt Subscriber Agreement has changed:\n  %s\n", agreementURL)
 		fmt.Print("Do you agree to the new terms? (y/n): ")
 	} else {
-		fmt.Printf("To continue, you must agree to the Let's Encrypt Subscriber Agreement:\n%s\n", agreementURL)
+		fmt.Printf("To continue, you must agree to the Let's Encrypt Subscriber Agreement:\n  %s\n", agreementURL)
 		fmt.Print("Do you agree to the terms? (y/n): ")
 	}
 
@@ -191,3 +191,6 @@ var stdin = io.ReadWriter(os.Stdin)
 // The name of the folder for accounts where the email
 // address was not provided; default 'username' if you will.
 const emptyEmail = "default"
+
+// TODO: Use latest
+const saURL = "https://letsencrypt.org/documents/LE-SA-v1.0.1-July-27-2015.pdf"