diff --git a/cert/cert.go b/cert/cert.go
index 3429c82..bdf4834 100644
--- a/cert/cert.go
+++ b/cert/cert.go
@@ -36,6 +36,8 @@ import (
 	"path"
 	"strings"
 	"time"
+
+	"github.com/sirupsen/logrus"
 )
 
 const (
@@ -267,3 +269,14 @@ func ipsToStrings(ips []net.IP) []string {
 	}
 	return ss
 }
+
+// IsCertExpired checks if the certificate about to expire
+func IsCertExpired(cert *x509.Certificate) bool {
+	expirationDate := cert.NotAfter
+	diffDays := expirationDate.Sub(time.Now()).Hours() / 24.0
+	if diffDays <= 90 {
+		logrus.Infof("certificate will expire in %f days", diffDays)
+		return true
+	}
+	return false
+}
diff --git a/go.mod b/go.mod
index a5e6d2f..c1ca544 100644
--- a/go.mod
+++ b/go.mod
@@ -4,11 +4,15 @@ go 1.12
 
 require (
 	github.com/hashicorp/golang-lru v0.5.1
+	github.com/kisielk/gotool v1.0.0 // indirect
 	github.com/konsorten/go-windows-terminal-sequences v1.0.2 // indirect
 	github.com/sirupsen/logrus v1.4.1
 	github.com/stretchr/testify v1.3.0 // indirect
+	github.com/stripe/safesql v0.2.0 // indirect
 	golang.org/x/crypto v0.0.0-20190506204251-e1dfcc566284
 	golang.org/x/net v0.0.0-20190503192946-f4e77d36d62c // indirect
 	golang.org/x/sys v0.0.0-20190509141414-a5b02f93d862 // indirect
 	golang.org/x/text v0.3.2 // indirect
+	mvdan.cc/interfacer v0.0.0-20180901003855-c20040233aed // indirect
+	mvdan.cc/lint v0.0.0-20170908181259-adc824a0674b // indirect
 )
diff --git a/go.sum b/go.sum
index d117bd2..7709128 100644
--- a/go.sum
+++ b/go.sum
@@ -3,6 +3,8 @@ github.com/davecgh/go-spew v1.1.1 h1:vj9j/u1bqnvCEfJOwUhtlOARqs3+rkHYY13jYWTU97c
 github.com/davecgh/go-spew v1.1.1/go.mod h1:J7Y8YcW2NihsgmVo/mv3lAwl/skON4iLHjSsI+c5H38=
 github.com/hashicorp/golang-lru v0.5.1 h1:0hERBMJE1eitiLkihrMvRVBYAkpHzc/J3QdDN+dAcgU=
 github.com/hashicorp/golang-lru v0.5.1/go.mod h1:/m3WP610KZHVQ1SGc6re/UDhFvYD7pJ4Ao+sR/qLZy8=
+github.com/kisielk/gotool v1.0.0 h1:AV2c/EiW3KqPNT9ZKl07ehoAGi4C5/01Cfbblndcapg=
+github.com/kisielk/gotool v1.0.0/go.mod h1:XhKaO+MFFWcvkIS/tQcRk01m1F5IRFswLeQ+oQHNcck=
 github.com/konsorten/go-windows-terminal-sequences v1.0.1 h1:mweAR1A6xJ3oS2pRaGiHgQ4OO8tzTaLawm8vnODuwDk=
 github.com/konsorten/go-windows-terminal-sequences v1.0.1/go.mod h1:T0+1ngSBFLxvqU3pZ+m/2kptfBszLMUkC4ZK/EgS/cQ=
 github.com/konsorten/go-windows-terminal-sequences v1.0.2 h1:DB17ag19krx9CFsz4o3enTrPXyIXCl+2iCXH/aMAp9s=
@@ -17,6 +19,8 @@ github.com/stretchr/testify v1.2.2 h1:bSDNvY7ZPG5RlJ8otE/7V6gMiyenm9RtJ7IUVIAoJ1
 github.com/stretchr/testify v1.2.2/go.mod h1:a8OnRcib4nhh0OaRAV+Yts87kKdq0PP7pXfy6kDkUVs=
 github.com/stretchr/testify v1.3.0 h1:TivCn/peBQ7UY8ooIcPgZFpTNSz0Q2U6UrFlUfqbe0Q=
 github.com/stretchr/testify v1.3.0/go.mod h1:M5WIy9Dh21IEIfnGCwXGc5bZfKNJtfHm1UVUgZn+9EI=
+github.com/stripe/safesql v0.2.0 h1:xiefmCDd8c35PVSGrL2FhBiaKxviXnGziBDOpOejeBE=
+github.com/stripe/safesql v0.2.0/go.mod h1:q7b2n0JmzM1mVGfcYpanfVb2j23cXZeWFxcILPn3JV4=
 golang.org/x/crypto v0.0.0-20190308221718-c2843e01d9a2/go.mod h1:djNgcEr1/C05ACkg1iLfiJU5Ep61QUkGW8qpdssI0+w=
 golang.org/x/crypto v0.0.0-20190506204251-e1dfcc566284 h1:rlLehGeYg6jfoyz/eDqDU1iRXLKfR42nnNh57ytKEWo=
 golang.org/x/crypto v0.0.0-20190506204251-e1dfcc566284/go.mod h1:yigFU9vqHzYiE8UmvKecakEJjdnWj3jj499lnFckfCI=
@@ -35,4 +39,9 @@ golang.org/x/text v0.3.0 h1:g61tztE5qeGQ89tm6NTjjM9VPIm088od1l6aSorWRWg=
 golang.org/x/text v0.3.0/go.mod h1:NqM8EUOU14njkJ3fqMW+pc6Ldnwhi/IjpwHt7yyuwOQ=
 golang.org/x/text v0.3.2 h1:tW2bmiBqwgJj/UpqtC8EpXEZVYOwU0yG4iWbprSVAcs=
 golang.org/x/text v0.3.2/go.mod h1:bEr9sfX3Q8Zfm5fL9x+3itogRgK3+ptLWKqgva+5dAk=
+golang.org/x/tools v0.0.0-20180917221912-90fa682c2a6e h1:FDhOuMEY4JVRztM/gsbk+IKUQ8kj74bxZrgw87eMMVc=
 golang.org/x/tools v0.0.0-20180917221912-90fa682c2a6e/go.mod h1:n7NCudcB/nEzxVGmLbDWY5pfWTLqBcC2KZ6jyYvM4mQ=
+mvdan.cc/interfacer v0.0.0-20180901003855-c20040233aed h1:WX1yoOaKQfddO/mLzdV4wptyWgoH/6hwLs7QHTixo0I=
+mvdan.cc/interfacer v0.0.0-20180901003855-c20040233aed/go.mod h1:Xkxe497xwlCKkIaQYRfC7CSLworTXY9RMqwhhCm+8Nc=
+mvdan.cc/lint v0.0.0-20170908181259-adc824a0674b h1:DxJ5nJdkhDlLok9K6qO+5290kphDJbHOQO1DFFFTeBo=
+mvdan.cc/lint v0.0.0-20170908181259-adc824a0674b/go.mod h1:2odslEg/xrtNQqCYg2/jCoyKnw3vv5biOc3JnIcYfL4=
diff --git a/server.go b/server.go
index ca43086..2c01dbf 100644
--- a/server.go
+++ b/server.go
@@ -211,20 +211,25 @@ func (s *server) Update(status *ListenerStatus) (_err error) {
 	if tlsCert != nil {
 		s.tlsCert = tlsCert
 		for i, certBytes := range tlsCert.Certificate {
-			cert, err := x509.ParseCertificate(certBytes)
+			parsedCert, err := x509.ParseCertificate(certBytes)
 			if err != nil {
 				logrus.Errorf("Update cert %d parse error: %s", i, err)
 				s.tlsCert = nil
 				break
 			}
-
+			isExpired := cert.IsCertExpired(parsedCert)
+			if isExpired {
+				logrus.Infof("certificate is about to expire")
+				s.tlsCert = nil
+				break
+			}
 			ips := map[string]bool{}
-			for _, ip := range cert.IPAddresses {
+			for _, ip := range parsedCert.IPAddresses {
 				ips[ip.String()] = true
 			}
 
 			domains := map[string]bool{}
-			for _, domain := range cert.DNSNames {
+			for _, domain := range parsedCert.DNSNames {
 				domains[domain] = true
 			}