diff --git a/go.mod b/go.mod
index 3e3a018d8d..d980ba30f5 100644
--- a/go.mod
+++ b/go.mod
@@ -37,9 +37,9 @@ require (
 	github.com/urfave/cli v1.22.2
 	github.com/zclconf/go-cty v1.2.0
 	golang.org/x/crypto v0.0.0-20200622213623-75b288015ac9
-	golang.org/x/net v0.0.0-20200707034311-ab3426394381
+	golang.org/x/net v0.0.0-20201021035429-f5854403a974
 	golang.org/x/oauth2 v0.0.0-20200107190931-bf48bf16ab8d
-	golang.org/x/tools v0.0.0-20200113040837-eac381796e91 // indirect
+	golang.org/x/tools v0.0.0-20201110201400-7099162a900a // indirect
 	google.golang.org/api v0.15.0
 	google.golang.org/genproto v0.0.0-20200526211855-cb27e3aa2013
 	k8s.io/api v0.19.3
diff --git a/go.sum b/go.sum
index 57b7d5fae6..f6b41b1887 100644
--- a/go.sum
+++ b/go.sum
@@ -429,6 +429,7 @@ github.com/xiang90/probing v0.0.0-20190116061207-43a291ad63a2/go.mod h1:UETIi67q
 github.com/xordataexchange/crypt v0.0.3-0.20170626215501-b2862e3d0a77/go.mod h1:aYKd//L2LvnjZzWKhF00oedf4jCCReLcmhLdhm1A27Q=
 github.com/zclconf/go-cty v1.2.0 h1:sPHsy7ADcIZQP3vILvTjrh74ZA175TFP5vqiNK1UmlI=
 github.com/zclconf/go-cty v1.2.0/go.mod h1:hOPWgoHbaTUnI5k4D2ld+GRpFJSCe6bCM7m1q/N4PQ8=
+github.com/yuin/goldmark v1.2.1/go.mod h1:3hX8gzYuyVAZsxl0MRgGTJEmQBFcNTphYh9decYSb74=
 go.etcd.io/bbolt v1.3.3/go.mod h1:IbVyRI1SCnLcuJnV2u8VeU0CEYM7e686BmAb1XKL+uU=
 go.etcd.io/etcd v0.0.0-20191023171146-3cf2f69b5738/go.mod h1:dnLIgRNXwCJa5e+c6mIZCrds/GIG4ncV9HhK5PX7jPg=
 go.opencensus.io v0.21.0/go.mod h1:mSImk1erAIZhrmZN+AvHh14ztQfjbGwt4TtuofqLduU=
@@ -474,6 +475,8 @@ golang.org/x/mobile v0.0.0-20190719004257-d2bd2a29d028/go.mod h1:E/iHnbuqvinMTCc
 golang.org/x/mod v0.0.0-20190513183733-4bf6d317e70e/go.mod h1:mXi4GBBbnImb6dmsKGUJ2LatrhH/nqhxcFungHvyanc=
 golang.org/x/mod v0.1.0/go.mod h1:0QHyrYULN0/3qlju5TqG8bIK38QM8yzMo5ekMj3DlcY=
 golang.org/x/mod v0.1.1-0.20191105210325-c90efee705ee/go.mod h1:QqPTAvyqsEbceGzBzNggFXnrqF1CaUcvgkdR5Ot7KZg=
+golang.org/x/mod v0.3.0 h1:RM4zey1++hCTbCVQfnWeKs9/IEsaBLA8vTkd0WVtmH4=
+golang.org/x/mod v0.3.0/go.mod h1:s0Qsj1ACt9ePp/hMypM3fl4fZqREWJwdYDEqhRiZZUA=
 golang.org/x/net v0.0.0-20170114055629-f2499483f923/go.mod h1:mL1N/T3taQHkDXs73rZJwtUhF3w3ftmwwsq0BUmARs4=
 golang.org/x/net v0.0.0-20180724234803-3673e40ba225/go.mod h1:mL1N/T3taQHkDXs73rZJwtUhF3w3ftmwwsq0BUmARs4=
 golang.org/x/net v0.0.0-20180811021610-c39426892332/go.mod h1:mL1N/T3taQHkDXs73rZJwtUhF3w3ftmwwsq0BUmARs4=
@@ -500,6 +503,8 @@ golang.org/x/net v0.0.0-20191209160850-c0dbc17a3553/go.mod h1:z5CRVTTTmAJ677TzLL
 golang.org/x/net v0.0.0-20200324143707-d3edc9973b7e/go.mod h1:qpuaurCH72eLCgpAm/N6yyVIVM9cpaDIP3A8BGJEC5A=
 golang.org/x/net v0.0.0-20200707034311-ab3426394381 h1:VXak5I6aEWmAXeQjA+QSZzlgNrpq9mjcfDemuexIKsU=
 golang.org/x/net v0.0.0-20200707034311-ab3426394381/go.mod h1:/O7V0waA8r7cgGh81Ro3o1hOxt32SMVPicZroKQ2sZA=
+golang.org/x/net v0.0.0-20201021035429-f5854403a974 h1:IX6qOQeG5uLjB/hjjwjedwfjND0hgjPMMyO1RoIXQNI=
+golang.org/x/net v0.0.0-20201021035429-f5854403a974/go.mod h1:sp8m0HH+o8qH0wwXwYZr8TS3Oi6o0r6Gce1SSxlDquU=
 golang.org/x/oauth2 v0.0.0-20180821212333-d2e6202438be/go.mod h1:N/0e6XlmueqKjAGxoOufVs8QHGRruUQn6yWY3a++T0U=
 golang.org/x/oauth2 v0.0.0-20190226205417-e64efc72b421/go.mod h1:gOpvHmFTYa4IltrdGE7lF6nIHvwfUNPOp7c8zoXwtLw=
 golang.org/x/oauth2 v0.0.0-20190604053449-0f29369cfe45/go.mod h1:gOpvHmFTYa4IltrdGE7lF6nIHvwfUNPOp7c8zoXwtLw=
@@ -513,6 +518,7 @@ golang.org/x/sync v0.0.0-20190227155943-e225da77a7e6/go.mod h1:RxMgew5VJxzue5/jJ
 golang.org/x/sync v0.0.0-20190423024810-112230192c58/go.mod h1:RxMgew5VJxzue5/jJTE5uejpjVlOe/izrB70Jof72aM=
 golang.org/x/sync v0.0.0-20190911185100-cd5d95a43a6e h1:vcxGaoTs7kV8m5Np9uUNQin4BrLOthgV7252N8V+FwY=
 golang.org/x/sync v0.0.0-20190911185100-cd5d95a43a6e/go.mod h1:RxMgew5VJxzue5/jJTE5uejpjVlOe/izrB70Jof72aM=
+golang.org/x/sync v0.0.0-20201020160332-67f06af15bc9/go.mod h1:RxMgew5VJxzue5/jJTE5uejpjVlOe/izrB70Jof72aM=
 golang.org/x/sys v0.0.0-20170830134202-bb24a47a89ea/go.mod h1:STP8DvDyc/dI5b8T5hshtkjS+E42TnysNCUPdjciGhY=
 golang.org/x/sys v0.0.0-20180830151530-49385e6e1522/go.mod h1:STP8DvDyc/dI5b8T5hshtkjS+E42TnysNCUPdjciGhY=
 golang.org/x/sys v0.0.0-20180905080454-ebe1bf3edb33/go.mod h1:STP8DvDyc/dI5b8T5hshtkjS+E42TnysNCUPdjciGhY=
@@ -543,6 +549,7 @@ golang.org/x/sys v0.0.0-20191228213918-04cbcbbfeed8/go.mod h1:h1NjWce9XRLGQEsW7w
 golang.org/x/sys v0.0.0-20200323222414-85ca7c5b95cd/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
 golang.org/x/sys v0.0.0-20200622214017-ed371f2e16b4 h1:5/PjkGUjvEU5Gl6BxmvKRPpqo2uNMv4rcHBMwzk/st8=
 golang.org/x/sys v0.0.0-20200622214017-ed371f2e16b4/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
+golang.org/x/sys v0.0.0-20200930185726-fdedc70b468f/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
 golang.org/x/text v0.0.0-20160726164857-2910a502d2bf/go.mod h1:NqM8EUOU14njkJ3fqMW+pc6Ldnwhi/IjpwHt7yyuwOQ=
 golang.org/x/text v0.3.0/go.mod h1:NqM8EUOU14njkJ3fqMW+pc6Ldnwhi/IjpwHt7yyuwOQ=
 golang.org/x/text v0.3.1-0.20180807135948-17ff2d5776d2/go.mod h1:NqM8EUOU14njkJ3fqMW+pc6Ldnwhi/IjpwHt7yyuwOQ=
@@ -578,16 +585,23 @@ golang.org/x/tools v0.0.0-20190816200558-6889da9d5479/go.mod h1:b+2E5dAYhXwXZwtn
 golang.org/x/tools v0.0.0-20190911174233-4f2ddba30aff/go.mod h1:b+2E5dAYhXwXZwtnZ6UAqBI28+e2cm9otk0dWdXHAEo=
 golang.org/x/tools v0.0.0-20190920225731-5eefd052ad72/go.mod h1:b+2E5dAYhXwXZwtnZ6UAqBI28+e2cm9otk0dWdXHAEo=
 golang.org/x/tools v0.0.0-20191012152004-8de300cfc20a/go.mod h1:b+2E5dAYhXwXZwtnZ6UAqBI28+e2cm9otk0dWdXHAEo=
+golang.org/x/tools v0.0.0-20191119224855-298f0cb1881e/go.mod h1:b+2E5dAYhXwXZwtnZ6UAqBI28+e2cm9otk0dWdXHAEo=
 golang.org/x/tools v0.0.0-20191125144606-a911d9008d1f/go.mod h1:b+2E5dAYhXwXZwtnZ6UAqBI28+e2cm9otk0dWdXHAEo=
 golang.org/x/tools v0.0.0-20191205215504-7b8c8591a921/go.mod h1:b+2E5dAYhXwXZwtnZ6UAqBI28+e2cm9otk0dWdXHAEo=
 golang.org/x/tools v0.0.0-20191216052735-49a3e744a425/go.mod h1:TB2adYChydJhpapKDTa4BR/hXlZSLoq2Wpct/0txZ28=
 golang.org/x/tools v0.0.0-20191227053925-7b8e75db28f4/go.mod h1:TB2adYChydJhpapKDTa4BR/hXlZSLoq2Wpct/0txZ28=
 golang.org/x/tools v0.0.0-20200113040837-eac381796e91 h1:OOkytthzFBKHY5EfEgLUabprb0LtJVkQtNxAQ02+UE4=
 golang.org/x/tools v0.0.0-20200113040837-eac381796e91/go.mod h1:TB2adYChydJhpapKDTa4BR/hXlZSLoq2Wpct/0txZ28=
+golang.org/x/tools v0.0.0-20201105220310-78b158585360 h1:/9CzsU8hOpnSUCtem1vfWNgsVeCTgkMdx+VE5YIYxnU=
+golang.org/x/tools v0.0.0-20201105220310-78b158585360/go.mod h1:emZCQorbCU4vsT4fOWvOPXz4eW1wZW4PmDk9uLelYpA=
+golang.org/x/tools v0.0.0-20201110201400-7099162a900a h1:5E6TPwSBG74zT8xSrVc8W59K4ch4NFobVTnh2BYzHyU=
+golang.org/x/tools v0.0.0-20201110201400-7099162a900a/go.mod h1:emZCQorbCU4vsT4fOWvOPXz4eW1wZW4PmDk9uLelYpA=
 golang.org/x/xerrors v0.0.0-20190717185122-a985d3407aa7/go.mod h1:I/5z698sn9Ka8TeJc9MKroUUfqBBauWjQqLJ2OPfmY0=
 golang.org/x/xerrors v0.0.0-20191011141410-1b5146add898/go.mod h1:I/5z698sn9Ka8TeJc9MKroUUfqBBauWjQqLJ2OPfmY0=
 golang.org/x/xerrors v0.0.0-20191204190536-9bdfabe68543 h1:E7g+9GITq07hpfrRu66IVDexMakfv52eLZ2CXBWiKr4=
 golang.org/x/xerrors v0.0.0-20191204190536-9bdfabe68543/go.mod h1:I/5z698sn9Ka8TeJc9MKroUUfqBBauWjQqLJ2OPfmY0=
+golang.org/x/xerrors v0.0.0-20200804184101-5ec99f83aff1 h1:go1bK/D/BFZV2I8cIQd1NKEZ+0owSTG1fDTci4IqFcE=
+golang.org/x/xerrors v0.0.0-20200804184101-5ec99f83aff1/go.mod h1:I/5z698sn9Ka8TeJc9MKroUUfqBBauWjQqLJ2OPfmY0=
 gonum.org/v1/gonum v0.0.0-20190331200053-3d26580ed485/go.mod h1:2ltnJ7xHfj0zHS40VVPYEAAMTa3ZGguvHGBSJeRWqE0=
 gonum.org/v1/netlib v0.0.0-20190313105609-8cb42192e0e0/go.mod h1:wa6Ws7BG/ESfp6dHfk7C6KdzKA7wR7u/rKwOGE66zvw=
 gonum.org/v1/netlib v0.0.0-20190331212654-76723241ea4e/go.mod h1:kS+toOQn6AQKjmKJ7gzohV1XkqsFehRA2FbsbkopSuQ=
diff --git a/modules/ssh/ssh.go b/modules/ssh/ssh.go
index dfbeafed49..e6b220b9e1 100644
--- a/modules/ssh/ssh.go
+++ b/modules/ssh/ssh.go
@@ -14,6 +14,7 @@ import (
 
 	"github.com/gruntwork-io/terratest/modules/files"
 	"github.com/gruntwork-io/terratest/modules/logger"
+	"github.com/gruntwork-io/terratest/modules/retry"
 	"github.com/gruntwork-io/terratest/modules/testing"
 	"github.com/hashicorp/go-multierror"
 	"golang.org/x/crypto/ssh"
@@ -199,6 +200,33 @@ func CheckSshConnectionE(t testing.TestingT, host Host) error {
 	return err
 }
 
+// CheckSshConnectionWithRetry attempts to connect via SSH until max retries has been exceeded and fails the test
+// if the connection fails
+func CheckSshConnectionWithRetry(t testing.TestingT, host Host, retries int, sleepBetweenRetries time.Duration, f ...func(testing.TestingT, Host) error) {
+	handler := CheckSshConnectionE
+	if f != nil {
+		handler = f[0]
+	}
+	err := CheckSshConnectionWithRetryE(t, host, retries, sleepBetweenRetries, handler)
+	if err != nil {
+		t.Fatal(err)
+	}
+}
+
+// CheckSshConnectionWithRetryE attempts to connect via SSH until max retries has been exceeded and returns an error if
+// the connection fails
+func CheckSshConnectionWithRetryE(t testing.TestingT, host Host, retries int, sleepBetweenRetries time.Duration, f ...func(testing.TestingT, Host) error) error {
+	handler := CheckSshConnectionE
+	if f != nil {
+		handler = f[0]
+	}
+	_, err := retry.DoWithRetryE(t, fmt.Sprintf("Checking SSH connection to %s", host.Hostname), retries, sleepBetweenRetries, func() (string, error) {
+		return "", handler(t, host)
+	})
+
+	return err
+}
+
 // CheckSshCommand checks that you can connect via SSH to the given host and run the given command. Returns the stdout/stderr.
 func CheckSshCommand(t testing.TestingT, host Host, command string) string {
 	out, err := CheckSshCommandE(t, host, command)
diff --git a/modules/ssh/ssh_test.go b/modules/ssh/ssh_test.go
index 147f77f5a9..6f2ddd3c58 100644
--- a/modules/ssh/ssh_test.go
+++ b/modules/ssh/ssh_test.go
@@ -1,8 +1,11 @@
 package ssh
 
 import (
+	"errors"
+	"fmt"
 	"testing"
 
+	grunttest "github.com/gruntwork-io/terratest/modules/testing"
 	"github.com/stretchr/testify/assert"
 )
 
@@ -22,3 +25,27 @@ func TestHostWithCustomPort(t *testing.T) {
 
 	assert.Equal(t, customPort, host.getPort(), "host.getPort() did not return the custom port number")
 }
+
+func TestCheckSSHConnectionWithRetryE(t *testing.T) {
+	timesCalled = 0
+	host := Host{Hostname: "Host"}
+	assert.Nil(t, CheckSshConnectionWithRetryE(t, host, 10, 3, mockSshConnectionE))
+}
+
+func TestCheckSshConnectionWithRetry(t *testing.T) {
+	timesCalled = 0
+	host := Host{Hostname: "Host"}
+	CheckSshConnectionWithRetry(t, host, 10, 3, mockSshConnectionE)
+}
+
+var timesCalled int
+
+func mockSshConnectionE(t grunttest.TestingT, host Host) error {
+	timesCalled += 1
+	fmt.Println()
+	if timesCalled >= 5 {
+		return nil
+	} else {
+		return errors.New(fmt.Sprintf("Called %v times", timesCalled))
+	}
+}