diff --git a/pkg/minikube/logs/logs.go b/pkg/minikube/logs/logs.go
index 3d4391551aab..c181a88a6afa 100644
--- a/pkg/minikube/logs/logs.go
+++ b/pkg/minikube/logs/logs.go
@@ -33,7 +33,7 @@ import (
 )
 
 // rootCauseRe is a regular expression that matches known failure root causes
-var rootCauseRe = regexp.MustCompile(`^error: |eviction manager: pods.* evicted|unknown flag: --|forbidden.*no providers available|eviction manager:.*evicted`)
+var rootCauseRe = regexp.MustCompile(`^error: |eviction manager: pods.* evicted|unknown flag: --|forbidden.*no providers available|eviction manager:.*evicted|tls: bad certificate`)
 
 // ignoreRe is a regular expression that matches spurious errors to not surface
 var ignoreCauseRe = regexp.MustCompile("error: no objects passed to apply")
diff --git a/pkg/minikube/logs/logs_test.go b/pkg/minikube/logs/logs_test.go
index 85576a9a16ca..417f788fa039 100644
--- a/pkg/minikube/logs/logs_test.go
+++ b/pkg/minikube/logs/logs_test.go
@@ -34,6 +34,7 @@ func TestIsProblem(t *testing.T) {
 		{"apiserver-admission #3524", true, "error: unknown flag: --GenericServerRunOptions.AdmissionControl"},
 		{"no-providers-available #3818", true, ` kubelet.go:1662] Failed creating a mirror pod for "kube-apiserver-minikube_kube-system(c7d572aebd3d33b17fa78ae6395b6d0a)": pods "kube-apiserver-minikube" is forbidden: no providers available to validate pod request`},
 		{"no-objects-passed-to-apply #4010", false, "error: no objects passed to apply"},
+		{"bad-certificate #4251", true, "log.go:172] http: TLS handshake error from 127.0.0.1:49200: remote error: tls: bad certificate"},
 	}
 	for _, tc := range tests {
 		t.Run(tc.name, func(t *testing.T) {
diff --git a/pkg/minikube/problem/err_map.go b/pkg/minikube/problem/err_map.go
index a54d990a145c..6ccc3b8e368f 100644
--- a/pkg/minikube/problem/err_map.go
+++ b/pkg/minikube/problem/err_map.go
@@ -25,6 +25,12 @@ func re(s string) *regexp.Regexp {
 
 // vmProblems are VM related problems
 var vmProblems = map[string]match{
+	"HYPERKIT_NO_IP": {
+		Regexp: re(`IP address never found in dhcp leases file Temporary Error: Could not find an IP address for`),
+		Advice: "Install the latest minikube hyperkit driver, and run 'minikube delete'",
+		URL:    "https://github.com/kubernetes/minikube/blob/master/docs/drivers.md#hyperkit-driver",
+		Issues: []int{1926, 4206},
+	},
 	"VBOX_NOT_FOUND": {
 		Regexp: re(`VBoxManage not found. Make sure VirtualBox is installed and VBoxManage is in the path`),
 		Advice: "Install VirtualBox, ensure that VBoxManage is executable and in path, or select an alternative value for --vm-driver",
@@ -67,7 +73,7 @@ var vmProblems = map[string]match{
 	"VBOX_HOST_ADAPTER": {
 		Regexp: re(`The host-only adapter we just created is not visible`),
 		Advice: "Reboot to complete VirtualBox installation, and verify that VirtualBox is not blocked by your system",
-		Issues: []int{3614},
+		Issues: []int{3614, 4222},
 		URL:    "https://stackoverflow.com/questions/52277019/how-to-fix-vm-issue-with-minikube-start",
 	},
 	"VBOX_KERNEL_MODULE_NOT_LOADED": {
@@ -80,10 +86,16 @@ var vmProblems = map[string]match{
 		Advice: "Please install the minikube kvm2 VM driver, or select an alternative --vm-driver",
 		URL:    "https://github.com/kubernetes/minikube/blob/master/docs/drivers.md#kvm2-driver",
 	},
-	"KVM2_NO_IP": {
+	"KVM2_RESTART_NO_IP": {
 		Regexp: re(`Error starting stopped host: Machine didn't return an IP after 120 seconds`),
 		Advice: "The KVM driver is unable to resurrect this old VM. Please run `minikube delete` to delete it and try again.",
-		Issues: []int{3901, 3566, 3434},
+		Issues: []int{3901, 3434},
+	},
+	"KVM2_START_NO_IP": {
+		Regexp: re(`Error in driver during machine creation: Machine didn't return an IP after 120 seconds`),
+		Advice: "The KVM driver is not providing an IP address to the VM. Try checking your libvirt configuration and/or opening an issue",
+		URL:    "https://fedoraproject.org/wiki/How_to_debug_Virtualization_problems#Networking",
+		Issues: []int{4249, 3566},
 	},
 	"KVM2_NETWORK_DEFINE_XML": {
 		Regexp: re(`not supported by the connection driver: virNetworkDefineXML`),
@@ -91,10 +103,11 @@ var vmProblems = map[string]match{
 		URL:    "https://forums.gentoo.org/viewtopic-t-981692-start-0.html",
 		Issues: []int{4195},
 	},
-	"VM_DOES_NOT_EXIST": {
-		Regexp: re(`Error getting state for host: machine does not exist`),
-		Advice: "Your system no longer knows about the VM previously created by minikube. Run 'minikube delete' to reset your local state.",
-		Issues: []int{3864},
+	"KVM_UNAVAILABLE": {
+		Regexp: re(`invalid argument: could not find capabilities for domaintype=kvm`),
+		Advice: "Your host does not support KVM virtualization. Ensure that qemu-kvm is installed, and run 'virt-host-validate' to debug the problem",
+		URL:    "http://mikko.repolainen.fi/documents/virtualization-with-kvm",
+		Issues: []int{2991},
 	},
 	"VM_BOOT_FAILED_HYPERV_ENABLED": {
 		Regexp: re(`VirtualBox won't boot a 64bits VM when Hyper-V is activated`),
@@ -106,6 +119,21 @@ var vmProblems = map[string]match{
 		Advice: "Configure an external network switch following the official documentation, then add `--hyperv-virtual-switch=<switch-name>` to `minikube start`",
 		URL:    "https://docs.docker.com/machine/drivers/hyper-v/",
 	},
+	"HOST_CIDR_CONFLICT": {
+		Regexp: re(`host-only cidr conflicts with the network address of a host interface`),
+		Advice: "Specify an alternate --host-only-cidr value, such as 172.16.0.1/24",
+		Issues: []int{3594},
+	},
+	"OOM_KILL_SSH": {
+		Regexp: re(`Process exited with status 137 from signal KILL`),
+		Advice: "Disable dynamic memory in your VM manager, or pass in a larger --memory value",
+		Issues: []int{1766},
+	},
+	"OOM_KILL_SCP": {
+		Regexp: re(`An existing connection was forcibly closed by the remote host`),
+		Advice: "Disable dynamic memory in your VM manager, or pass in a larger --memory value",
+		Issues: []int{1766},
+	},
 }
 
 // proxyDoc is the URL to proxy documentation
@@ -132,10 +160,10 @@ var netProblems = map[string]match{
 		Issues: []int{3846},
 	},
 	"DOWNLOAD_TLS_OVERSIZED": {
-		Regexp: re(`failed to download.*tls: oversized record received with length`),
-		Advice: "A firewall is interfering with minikube's ability to make outgoing HTTPS requests. You may need to configure minikube to use a proxy.",
+		Regexp: re(`tls: oversized record received with length`),
+		Advice: "A firewall is interfering with minikube's ability to make outgoing HTTPS requests. You may need to change the value of the HTTPS_PROXY environment variable.",
 		URL:    proxyDoc,
-		Issues: []int{3857, 3759},
+		Issues: []int{3857, 3759, 4252},
 	},
 	"ISO_DOWNLOAD_FAILED": {
 		Regexp: re(`iso: failed to download`),
@@ -181,6 +209,11 @@ var deployProblems = map[string]match{
 		Regexp: re(`strconv.ParseUint: parsing "": invalid syntax`),
 		Advice: "Check that your --kubernetes-version has a leading 'v'. For example: 'v1.1.14'",
 	},
+	"APISERVER_TIMEOUT": {
+		Regexp: re(`wait: waiting for component=kube-apiserver: timed out waiting for the condition`),
+		Advice: "Run 'minikube delete'. If the problem persists, check your proxy or firewall configuration",
+		Issues: []int{4202, 3836, 4221},
+	},
 }
 
 // osProblems are operating-system specific issues
@@ -190,6 +223,12 @@ var osProblems = map[string]match{
 		Advice: "Run minikube from the C: drive.",
 		Issues: []int{1574},
 	},
+	"SYSTEMCTL_EXIT_1": {
+		Regexp: re(`Failed to enable container runtime: .*sudo systemctl start docker: exit status 1`),
+		Advice: "If using the none driver, ensure that systemctl is installed",
+		URL:    "https://github.com/kubernetes/minikube/blob/master/docs/vmdriver-none.md",
+		Issues: []int{2704},
+	},
 }
 
 // stateProblems are issues relating to local state
diff --git a/pkg/minikube/problem/problem_test.go b/pkg/minikube/problem/problem_test.go
index 85738ffbdb5f..75ffa8a1d604 100644
--- a/pkg/minikube/problem/problem_test.go
+++ b/pkg/minikube/problem/problem_test.go
@@ -29,6 +29,8 @@ func TestFromError(t *testing.T) {
 		err   string
 	}{
 		{0, "", "", "this is just a lame error message with no matches."},
+		{2991, "", "KVM_UNAVAILABLE", "Unable to start VM: create: Error creating machine: Error in driver during machine creation: creating domain: Error defining domain xml:\n\n: virError(Code=8, Domain=44, Message='invalid argument: could not find capabilities for domaintype=kvm ')"},
+		{3594, "", "HOST_CIDR_CONFLICT", "Error starting host: Error starting stopped host: Error setting up host only network on machine start: host-only cidr conflicts with the network address of a host interface."},
 		{3614, "", "VBOX_HOST_ADAPTER", "Error starting host:  Error starting stopped host: Error setting up host only network on machine start: The host-only adapter we just created is not visible. This is a well known VirtualBox bug. You might want to uninstall it and reinstall at least version 5.0.12 that is is supposed to fix this issue"},
 		{3784, "", "VBOX_NOT_FOUND", "create: precreate: VBoxManage not found. Make sure VirtualBox is installed and VBoxManage is in the path"},
 		{3849, "", "IP_NOT_FOUND", "bootstrapper: Error creating new ssh host from driver: Error getting ssh host name for driver: IP not found"},
@@ -38,6 +40,9 @@ VBoxManage.exe: error: Details: code E_FAIL (0x80004005), component MachineWrap,
 		{3922, "", "ISO_DOWNLOAD_FAILED", `unable to cache ISO: https://storage.googleapis.com/minikube/iso/minikube-v0.35.0.iso: failed to download: failed to download to temp file: download failed: 5 error(s) occurred:
 * Temporary download error: Get https://storage.googleapis.com/minikube/iso/minikube-v0.35.0.iso: dial tcp 216.58.207.144:443: connectex: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.`},
 		{4107, "darwin", "VBOX_BLOCKED", "Result Code: NS_ERROR_FAILURE (0x80004005)"},
+		{4202, "", "APISERVER_TIMEOUT", "Error restarting cluster: wait: waiting for component=kube-apiserver: timed out waiting for the condition"},
+		{4252, "", "DOWNLOAD_TLS_OVERSIZED", "Failed to update cluster: downloading binaries: downloading kubeadm: Error downloading kubeadm v1.14.1: failed to download: failed to download to temp file: download failed: 5 error(s) occurred:\n\nTemporary download error: Get https://storage.googleapis.com/kubernetes-release/release/v1.14.1/bin/linux/amd64/kubeadm: proxyconnect tcp: tls: oversized record received with length 20527"},
+		{4222, "", "VBOX_HOST_ADAPTER", "Unable to start VM: create: creating: Error setting up host only network on machine start: The host-only adapter we just created is not visible. This is a well known VirtualBox bug. You might want to uninstall it and reinstall at least version 5.0.12 that is is supposed to fix this issue"},
 	}
 	for _, tc := range tests {
 		t.Run(tc.want, func(t *testing.T) {