diff --git a/pkg/minikube/exit/exit.go b/pkg/minikube/exit/exit.go
index b0908fbf5bd0..bb18b02ca40a 100644
--- a/pkg/minikube/exit/exit.go
+++ b/pkg/minikube/exit/exit.go
@@ -20,6 +20,7 @@ package exit
 import (
 	"fmt"
 	"os"
+	"runtime"
 
 	"github.com/golang/glog"
 	"k8s.io/minikube/pkg/minikube/console"
@@ -59,7 +60,7 @@ func WithCode(code int, format string, a ...interface{}) {
 
 // WithError outputs an error and exits.
 func WithError(msg string, err error) {
-	p := problem.FromError(err)
+	p := problem.FromError(err, runtime.GOOS)
 	if p != nil {
 		WithProblem(msg, p)
 	}
diff --git a/pkg/minikube/problem/err_map.go b/pkg/minikube/problem/err_map.go
index a595a93009f2..bf0caf58d01c 100644
--- a/pkg/minikube/problem/err_map.go
+++ b/pkg/minikube/problem/err_map.go
@@ -36,10 +36,49 @@ var vmProblems = map[string]match{
 		Advice: "In some environments, this message is incorrect. Try 'minikube start --no-vtx-check'",
 		Issues: []int{3900},
 	},
-	"VBOX_THIRD_PARTY": {
-		Regexp: re(`The virtual machine * has terminated unexpectedly during startup with exit code 1`),
-		Advice: "A third-party program may be interfering with VirtualBox. Try disabling any real-time antivirus software, reinstalling VirtualBox and rebooting.",
-		Issues: []int{3910},
+	"VBOX_VERR_VMX_NO_VMX": {
+		Regexp: re(`VT-x is not available.*VERR_VMX_NO_VMX`),
+		Advice: "Please check your BIOS, and ensure that you are running without HyperV or other nested virtualization that may interfere",
+		Issues: []int{1994},
+	},
+	"VBOX_BLOCKED": {
+		Regexp: re(`NS_ERROR_FAILURE.*0x80004005`),
+		Advice: "Reinstall VirtualBox and verify that it is not blocked: System Preferences -> Security & Privacy -> General -> Some system software was blocked from loading",
+		Issues: []int{4107},
+		GOOS:   "darwin",
+	},
+	"VBOX_DRV_NOT_LOADED": {
+		Regexp: re(`The vboxdrv kernel module is not loaded`),
+		Advice: "Run 'sudo modprobe vboxdrv' and reinstall VirtualBox if it fails.",
+		Issues: []int{4043},
+	},
+	"VBOX_DEVICE_MISSING": {
+		Regexp: re(`/dev/vboxdrv does not exist`),
+		Advice: "Run 'sudo modprobe vboxdrv' and reinstall VirtualBox if it fails.",
+		Issues: []int{3974},
+	},
+	"VBOX_HARDENING": {
+		Regexp: re(`terminated unexpectedly.*VBoxHardening`),
+		Advice: "Disable real-time anti-virus software, reboot, and reinstall VirtualBox if the problem continues.",
+		Issues: []int{3859, 3910},
+		URL:    "https://forums.virtualbox.org/viewtopic.php?f=25&t=82106",
+		GOOS:   "windows",
+	},
+	"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},
+		URL:    "https://stackoverflow.com/questions/52277019/how-to-fix-vm-issue-with-minikube-start",
+	},
+	"VBOX_BLOCKED_LOADING": {
+		Regexp: re(`NS_ERROR_FAILURE.*0x80004005`),
+		Advice: "Reinstall VirtualBox and verify that it is not blocked: System Preferences -> Security & Privacy -> General -> Some system software was blocked from loading",
+		Issues: []int{4107},
+	},
+	"VBOX_KERNEL_MODULE_NOT_LOADED": {
+		Regexp: re(`The vboxdrv kernel module is not loaded`),
+		Advice: "Run 'sudo modprobe vboxdrv' and reinstall VirtualBox if it fails.",
+		Issues: []int{4043},
 	},
 	"KVM2_NOT_FOUND": {
 		Regexp: re(`Driver "kvm2" not found. Do you have the plugin binary .* accessible in your PATH`),
@@ -51,16 +90,17 @@ var vmProblems = map[string]match{
 		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},
 	},
+	"KVM2_NETWORK_DEFINE_XML": {
+		Regexp: re(`not supported by the connection driver: virNetworkDefineXML`),
+		Advice: "Rebuild libvirt with virt-network support",
+		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},
 	},
-	"VM_IP_NOT_FOUND": {
-		Regexp: re(`Error getting ssh host name for driver: IP not found`),
-		Advice: "The minikube VM is offline. Please run 'minikube start' to start it again.",
-		Issues: []int{3849, 3648},
-	},
 	"VM_BOOT_FAILED_HYPERV_ENABLED": {
 		Regexp: re(`VirtualBox won't boot a 64bits VM when Hyper-V is activated`),
 		Advice: "Disable Hyper-V when you want to run VirtualBox to boot the VM",
@@ -156,3 +196,17 @@ var osProblems = map[string]match{
 		Issues: []int{1574},
 	},
 }
+
+// stateProblems are issues relating to local state
+var stateProblems = map[string]match{
+	"MACHINE_DOES_NOT_EXST": {
+		Regexp: re(`Error getting state for host: machine does not exist`),
+		Advice: "Run 'minikube delete' to delete the stale VM",
+		Issues: []int{3864},
+	},
+	"IP_NOT_FOUND": {
+		Regexp: re(`Error getting ssh host name for driver: IP not found`),
+		Advice: "The minikube VM is offline. Please run 'minikube start' to start it again.",
+		Issues: []int{3849, 3648},
+	},
+}
diff --git a/pkg/minikube/problem/problem.go b/pkg/minikube/problem/problem.go
index e5184341f8ab..446e16e940f5 100644
--- a/pkg/minikube/problem/problem.go
+++ b/pkg/minikube/problem/problem.go
@@ -27,10 +27,15 @@ const issueBase = "https://github.com/kubernetes/minikube/issues"
 
 // Problem represents a known problem in minikube.
 type Problem struct {
-	ID     string
-	Err    error
+	// ID is an arbitrary unique and stable string describing this issue
+	ID string
+	// Err is the original error
+	Err error
+	// Advice is actionable text that the user should follow
 	Advice string
-	URL    string
+	// URL is a reference URL for more information
+	URL string
+	// Issues are a list of related issues to this problem
 	Issues []int
 }
 
@@ -40,6 +45,8 @@ type match struct {
 	Advice string
 	URL    string
 	Issues []int
+	// GOOS is what platforms this problem may be specific to, when disambiguation is necessary.
+	GOOS string
 }
 
 // Display problem metadata to the console
@@ -62,16 +69,20 @@ func (p *Problem) Display() {
 	}
 }
 
-// FromError returns a known problem from an error.
-func FromError(err error) *Problem {
+// FromError returns a known problem from an error on an OS
+func FromError(err error, os string) *Problem {
 	maps := []map[string]match{
 		osProblems,
 		vmProblems,
 		netProblems,
 		deployProblems,
+		stateProblems,
 	}
 	for _, m := range maps {
 		for k, v := range m {
+			if v.GOOS != "" && v.GOOS != os {
+				continue
+			}
 			if v.Regexp.MatchString(err.Error()) {
 				return &Problem{
 					Err:    err,
diff --git a/pkg/minikube/problem/problem_test.go b/pkg/minikube/problem/problem_test.go
new file mode 100644
index 000000000000..85738ffbdb5f
--- /dev/null
+++ b/pkg/minikube/problem/problem_test.go
@@ -0,0 +1,66 @@
+/*
+Copyright 2019 The Kubernetes Authors All rights reserved.
+
+Licensed under the Apache License, Version 2.0 (the "License");
+you may not use this file except in compliance with the License.
+You may obtain a copy of the License at
+
+    http://www.apache.org/licenses/LICENSE-2.0
+
+Unless required by applicable law or agreed to in writing, software
+distributed under the License is distributed on an "AS IS" BASIS,
+WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+See the License for the specific language governing permissions and
+limitations under the License.
+*/
+
+package problem
+
+import (
+	"fmt"
+	"testing"
+)
+
+func TestFromError(t *testing.T) {
+	var tests = []struct {
+		issue int
+		os    string
+		want  string
+		err   string
+	}{
+		{0, "", "", "this is just a lame error message with no matches."},
+		{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"},
+		{3859, "windows", "VBOX_HARDENING", `Unable to start VM: create: creating: Unable to start the VM: C:\Program Files\Oracle\VirtualBox\VBoxManage.exe startvm minikube --type headless failed:
+VBoxManage.exe: error: The virtual machine 'minikube' has terminated unexpectedly during startup with exit code -1073741819 (0xc0000005). More details may be available in 'C:\Users\pabitra_b.minikube\machines\minikube\minikube\Logs\VBoxHardening.log'
+VBoxManage.exe: error: Details: code E_FAIL (0x80004005), component MachineWrap, interface IMachine`},
+		{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)"},
+	}
+	for _, tc := range tests {
+		t.Run(tc.want, func(t *testing.T) {
+			got := FromError(fmt.Errorf(tc.err), tc.os)
+			if got == nil {
+				if tc.want != "" {
+					t.Errorf("FromError(%q)=nil, want %s", tc.err, tc.want)
+				}
+				return
+			}
+			if got.ID != tc.want {
+				t.Errorf("FromError(%q)=%s, want %s", tc.err, got.ID, tc.want)
+			}
+
+			found := false
+			for _, i := range got.Issues {
+				if i == tc.issue {
+					found = true
+				}
+			}
+			if !found {
+				t.Errorf("Issue %d is not listed in %+v", tc.issue, got.Issues)
+			}
+		})
+	}
+}