diff --git a/cmd/openshift-install/main.go b/cmd/openshift-install/main.go
index c14d57095d3..8093ec46022 100644
--- a/cmd/openshift-install/main.go
+++ b/cmd/openshift-install/main.go
@@ -82,7 +82,7 @@ func main() {
 		for _, asset := range targetAssets {
 			st, err := assetStore.Fetch(asset)
 			if err != nil {
-				logrus.Fatalf("Failed to generate asset: %v", err)
+				logrus.Fatalf("Failed to generate %s: %v", asset.Name(), err)
 			}
 
 			if err := st.PersistToFile(*dirFlag); err != nil {
diff --git a/pkg/asset/asset.go b/pkg/asset/asset.go
index ec6884912fb..c3f3fe02c0d 100644
--- a/pkg/asset/asset.go
+++ b/pkg/asset/asset.go
@@ -1,8 +1,9 @@
 package asset
 
 import (
-	"fmt"
 	"path/filepath"
+
+	"github.com/pkg/errors"
 )
 
 // Asset used to install OpenShift.
@@ -22,7 +23,7 @@ type Asset interface {
 func GetDataByFilename(a Asset, parents map[Asset]*State, filename string) ([]byte, error) {
 	st, ok := parents[a]
 	if !ok {
-		return nil, fmt.Errorf("failed to find %T in parents", a)
+		return nil, errors.Errorf("failed to find %T in parents", a)
 	}
 
 	for _, c := range st.Contents {
@@ -30,5 +31,5 @@ func GetDataByFilename(a Asset, parents map[Asset]*State, filename string) ([]by
 			return c.Data, nil
 		}
 	}
-	return nil, fmt.Errorf("failed to find data in %v with filename == %q", st, filename)
+	return nil, errors.Errorf("failed to find data in %v with filename == %q", st, filename)
 }
diff --git a/pkg/asset/cluster/cluster.go b/pkg/asset/cluster/cluster.go
index 348d2b8e6fc..2222db57cde 100644
--- a/pkg/asset/cluster/cluster.go
+++ b/pkg/asset/cluster/cluster.go
@@ -2,11 +2,11 @@ package cluster
 
 import (
 	"encoding/json"
-	"fmt"
 	"io/ioutil"
 	"os"
 	"path/filepath"
 
+	"github.com/pkg/errors"
 	"github.com/sirupsen/logrus"
 
 	"github.com/openshift/installer/data"
@@ -45,23 +45,23 @@ func (c *Cluster) Dependencies() []asset.Asset {
 func (c *Cluster) Generate(parents map[asset.Asset]*asset.State) (*asset.State, error) {
 	state, ok := parents[c.tfvars]
 	if !ok {
-		return nil, fmt.Errorf("failed to get terraform.tfvar state in the parent asset states")
+		return nil, errors.Errorf("failed to get terraform.tfvars from parent")
 	}
 
 	// Copy the terraform.tfvars to a temp directory where the terraform will be invoked within.
 	tmpDir, err := ioutil.TempDir(os.TempDir(), "openshift-install-")
 	if err != nil {
-		return nil, fmt.Errorf("failed to create temp dir: %v", err)
+		return nil, errors.Wrap(err, "failed to create temp dir for terraform execution")
 	}
 	defer os.RemoveAll(tmpDir)
 
 	if err := ioutil.WriteFile(filepath.Join(tmpDir, state.Contents[0].Name), state.Contents[0].Data, 0600); err != nil {
-		return nil, fmt.Errorf("failed to write terraform.tfvars file: %v", err)
+		return nil, errors.Wrap(err, "failed to write terraform.tfvars file")
 	}
 
 	var tfvars config.Cluster
 	if err := json.Unmarshal(state.Contents[0].Data, &tfvars); err != nil {
-		return nil, fmt.Errorf("failed to unmarshal terraform tfvars file: %v", err)
+		return nil, errors.Wrap(err, "failed to Unmarshal terraform.tfvars file")
 	}
 
 	platform := string(tfvars.Platform)
@@ -78,12 +78,12 @@ func (c *Cluster) Generate(parents map[asset.Asset]*asset.State) (*asset.State,
 	// This runs the terraform in a temp directory, the tfstate file will be returned
 	// to the asset store to persist it on the disk.
 	if err := terraform.Init(tmpDir); err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to initialize terraform")
 	}
 
 	stateFile, err := terraform.Apply(tmpDir)
 	if err != nil {
-		err = fmt.Errorf("terraform failed: %v", err)
+		err = errors.Wrap(err, "failed to run terraform")
 	}
 
 	data, err2 := ioutil.ReadFile(stateFile)
diff --git a/pkg/asset/cluster/tfvars.go b/pkg/asset/cluster/tfvars.go
index a0709896ae1..5baf6a5582e 100644
--- a/pkg/asset/cluster/tfvars.go
+++ b/pkg/asset/cluster/tfvars.go
@@ -1,11 +1,10 @@
 package cluster
 
 import (
-	"fmt"
-
 	"github.com/openshift/installer/pkg/asset"
 	"github.com/openshift/installer/pkg/asset/installconfig"
 	"github.com/openshift/installer/pkg/types/config"
+	"github.com/pkg/errors"
 )
 
 const (
@@ -39,7 +38,7 @@ func (t *TerraformVariables) Dependencies() []asset.Asset {
 func (t *TerraformVariables) Generate(parents map[asset.Asset]*asset.State) (*asset.State, error) {
 	installCfg, err := installconfig.GetInstallConfig(t.installConfig, parents)
 	if err != nil {
-		return nil, fmt.Errorf("failed to get install config state in the parent asset states")
+		return nil, errors.Wrap(err, "failed to get InstallConfig from parents")
 	}
 
 	contents := map[asset.Asset][]string{}
@@ -51,7 +50,7 @@ func (t *TerraformVariables) Generate(parents map[asset.Asset]*asset.State) (*as
 	} {
 		state, ok := parents[ign]
 		if !ok {
-			return nil, fmt.Errorf("failed to get the ignition state for %v in the parent asset states", ign)
+			return nil, errors.Errorf("failed to get the ignition state for %v in the parent asset states", ign)
 		}
 
 		for _, content := range state.Contents {
@@ -72,7 +71,7 @@ func (t *TerraformVariables) Generate(parents map[asset.Asset]*asset.State) (*as
 
 	data, err := cluster.TFVars()
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get Tfvars")
 	}
 
 	return &asset.State{
diff --git a/pkg/asset/ignition/bootstrap/bootstrap.go b/pkg/asset/ignition/bootstrap/bootstrap.go
index 51e6fc9bad7..1ce9f5c8718 100644
--- a/pkg/asset/ignition/bootstrap/bootstrap.go
+++ b/pkg/asset/ignition/bootstrap/bootstrap.go
@@ -10,6 +10,7 @@ import (
 
 	"github.com/coreos/ignition/config/util"
 	igntypes "github.com/coreos/ignition/config/v2_2/types"
+	"github.com/pkg/errors"
 	log "github.com/sirupsen/logrus"
 
 	"github.com/openshift/installer/pkg/asset"
@@ -133,12 +134,12 @@ func (a *bootstrap) Dependencies() []asset.Asset {
 func (a *bootstrap) Generate(dependencies map[asset.Asset]*asset.State) (*asset.State, error) {
 	installConfig, err := installconfig.GetInstallConfig(a.installConfig, dependencies)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get InstallConfig from parents")
 	}
 
 	templateData, err := a.getTemplateData(installConfig)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get bootstrap templates")
 	}
 
 	config := igntypes.Config{
@@ -166,7 +167,7 @@ func (a *bootstrap) Generate(dependencies map[asset.Asset]*asset.State) (*asset.
 
 	data, err := json.Marshal(config)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to Marshal Ignition config")
 	}
 
 	return &asset.State{
@@ -186,7 +187,7 @@ func (a *bootstrap) Name() string {
 func (a *bootstrap) getTemplateData(installConfig *types.InstallConfig) (*bootstrapTemplateData, error) {
 	clusterDNSIP, err := installconfig.ClusterDNSIP(installConfig)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get ClusterDNSIP from InstallConfig")
 	}
 	etcdEndpoints := make([]string, installConfig.MasterCount())
 	for i := range etcdEndpoints {
diff --git a/pkg/asset/ignition/machine/master.go b/pkg/asset/ignition/machine/master.go
index b7e19dfbf4a..31c668d1080 100644
--- a/pkg/asset/ignition/machine/master.go
+++ b/pkg/asset/ignition/machine/master.go
@@ -3,6 +3,8 @@ package machine
 import (
 	"fmt"
 
+	"github.com/pkg/errors"
+
 	"github.com/openshift/installer/pkg/asset"
 	"github.com/openshift/installer/pkg/asset/installconfig"
 	"github.com/openshift/installer/pkg/asset/tls"
@@ -39,7 +41,7 @@ func (a *master) Dependencies() []asset.Asset {
 func (a *master) Generate(dependencies map[asset.Asset]*asset.State) (*asset.State, error) {
 	installConfig, err := installconfig.GetInstallConfig(a.installConfig, dependencies)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get InstallConfig from parents")
 	}
 
 	state := &asset.State{
diff --git a/pkg/asset/ignition/machine/worker.go b/pkg/asset/ignition/machine/worker.go
index 15b37c85385..2b92ffa6648 100644
--- a/pkg/asset/ignition/machine/worker.go
+++ b/pkg/asset/ignition/machine/worker.go
@@ -1,6 +1,8 @@
 package machine
 
 import (
+	"github.com/pkg/errors"
+
 	"github.com/openshift/installer/pkg/asset"
 	"github.com/openshift/installer/pkg/asset/installconfig"
 	"github.com/openshift/installer/pkg/asset/tls"
@@ -37,7 +39,7 @@ func (a *worker) Dependencies() []asset.Asset {
 func (a *worker) Generate(dependencies map[asset.Asset]*asset.State) (*asset.State, error) {
 	installConfig, err := installconfig.GetInstallConfig(a.installConfig, dependencies)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get InstallConfig from parents")
 	}
 
 	return &asset.State{
diff --git a/pkg/asset/installconfig/installconfig.go b/pkg/asset/installconfig/installconfig.go
index 79b7e769015..33a7833d86f 100644
--- a/pkg/asset/installconfig/installconfig.go
+++ b/pkg/asset/installconfig/installconfig.go
@@ -7,7 +7,7 @@ import (
 
 	"github.com/apparentlymart/go-cidr/cidr"
 	"github.com/ghodss/yaml"
-
+	"github.com/pkg/errors"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 
 	"github.com/openshift/installer/pkg/asset"
@@ -131,7 +131,7 @@ func (a *installConfig) Generate(dependencies map[asset.Asset]*asset.State) (*as
 
 	data, err := yaml.Marshal(installConfig)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to Marshal InstallConfig")
 	}
 
 	return &asset.State{
@@ -155,13 +155,12 @@ func GetInstallConfig(installConfig asset.Asset, parents map[asset.Asset]*asset.
 
 	st, ok := parents[installConfig]
 	if !ok {
-		return nil, fmt.Errorf("failed to find %T in parents", installConfig)
+		return nil, errors.Errorf("%T does not exist in parents", installConfig)
 	}
 
 	if err := yaml.Unmarshal(st.Contents[0].Data, &cfg); err != nil {
-		return nil, fmt.Errorf("failed to unmarshal the installconfig: %v", err)
+		return nil, errors.Wrap(err, "failed to Unmarshal the installconfig")
 	}
-
 	return &cfg, nil
 }
 
diff --git a/pkg/asset/installconfig/platform.go b/pkg/asset/installconfig/platform.go
index fcdbb68c4cc..c4bbebb81a2 100644
--- a/pkg/asset/installconfig/platform.go
+++ b/pkg/asset/installconfig/platform.go
@@ -8,6 +8,7 @@ import (
 	"sort"
 	"strings"
 
+	"github.com/pkg/errors"
 	survey "gopkg.in/AlecAivazis/survey.v1"
 
 	"github.com/openshift/installer/pkg/asset"
@@ -100,6 +101,7 @@ func (a *Platform) Name() string {
 func (a *Platform) queryUserForPlatform() (string, error) {
 	sort.Strings(validPlatforms)
 	prompt := asset.UserProvided{
+		AssetName: "Platform",
 		Question: &survey.Question{
 			Prompt: &survey.Select{
 				Message: "Platform",
@@ -109,7 +111,7 @@ func (a *Platform) queryUserForPlatform() (string, error) {
 				choice := ans.(string)
 				i := sort.SearchStrings(validPlatforms, choice)
 				if i == len(validPlatforms) || validPlatforms[i] != choice {
-					return fmt.Errorf("invalid platform %q", choice)
+					return errors.Errorf("invalid platform %q", choice)
 				}
 				return nil
 			}),
@@ -142,6 +144,7 @@ func (a *Platform) awsPlatform() (*asset.State, error) {
 	sort.Strings(longRegions)
 	sort.Strings(shortRegions)
 	prompt := asset.UserProvided{
+		AssetName: "AWS Region",
 		Question: &survey.Question{
 			Prompt: &survey.Select{
 				Message: "Region",
@@ -153,7 +156,7 @@ func (a *Platform) awsPlatform() (*asset.State, error) {
 				choice := regionTransform(ans).(string)
 				i := sort.SearchStrings(shortRegions, choice)
 				if i == len(shortRegions) || shortRegions[i] != choice {
-					return fmt.Errorf("invalid region %q", choice)
+					return errors.Errorf("invalid region %q", choice)
 				}
 				return nil
 			}),
@@ -169,13 +172,13 @@ func (a *Platform) awsPlatform() (*asset.State, error) {
 
 	if value, ok := os.LookupEnv("_CI_ONLY_STAY_AWAY_OPENSHIFT_INSTALL_AWS_USER_TAGS"); ok {
 		if err := json.Unmarshal([]byte(value), &platform.UserTags); err != nil {
-			return nil, fmt.Errorf("_CI_ONLY_STAY_AWAY_OPENSHIFT_INSTALL_AWS_USER_TAGS contains invalid JSON: %s (%v)", value, err)
+			return nil, errors.Wrapf(err, "_CI_ONLY_STAY_AWAY_OPENSHIFT_INSTALL_AWS_USER_TAGS contains invalid JSON: %s", value)
 		}
 	}
 
 	data, err := json.Marshal(platform)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrapf(err, "failed to Marshal %s platform", AWSPlatformType)
 	}
 
 	return &asset.State{
@@ -197,6 +200,7 @@ func (a *Platform) openstackPlatform() (*asset.State, error) {
 		NetworkCIDRBlock: defaultVPCCIDR,
 	}
 	prompt := asset.UserProvided{
+		AssetName: "OpenStack Region",
 		Question: &survey.Question{
 			Prompt: &survey.Select{
 				Message: "Region",
@@ -217,6 +221,7 @@ func (a *Platform) openstackPlatform() (*asset.State, error) {
 	}
 	platform.Region = string(region.Contents[0].Data)
 	prompt2 := asset.UserProvided{
+		AssetName: "OpenStack Image",
 		Question: &survey.Question{
 			Prompt: &survey.Select{
 				Message: "Image",
@@ -237,6 +242,7 @@ func (a *Platform) openstackPlatform() (*asset.State, error) {
 	}
 	platform.BaseImage = string(image.Contents[0].Data)
 	prompt3 := asset.UserProvided{
+		AssetName: "OpenStack Cloud",
 		Question: &survey.Question{
 			Prompt: &survey.Select{
 				Message: "Cloud",
@@ -256,6 +262,7 @@ func (a *Platform) openstackPlatform() (*asset.State, error) {
 	}
 	platform.Cloud = string(cloud.Contents[0].Data)
 	prompt4 := asset.UserProvided{
+		AssetName: "OpenStack External Network",
 		Question: &survey.Question{
 			Prompt: &survey.Select{
 				Message: "ExternalNetwork",
@@ -277,7 +284,7 @@ func (a *Platform) openstackPlatform() (*asset.State, error) {
 
 	data, err := json.Marshal(platform)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrapf(err, "failed to Marshal %s platform", OpenStackPlatformType)
 	}
 
 	return &asset.State{
@@ -307,6 +314,7 @@ func (a *Platform) libvirtPlatform() (*asset.State, error) {
 	}
 
 	uriPrompt := asset.UserProvided{
+		AssetName: "Libvirt Connection URI",
 		Question: &survey.Question{
 			Prompt: &survey.Input{
 				Message: "Libvirt Connection URI",
@@ -323,6 +331,7 @@ func (a *Platform) libvirtPlatform() (*asset.State, error) {
 	}
 
 	imagePrompt := asset.UserProvided{
+		AssetName: "Libvirt Image",
 		Question: &survey.Question{
 			Prompt: &survey.Input{
 				Message: "Image",
@@ -342,7 +351,7 @@ func (a *Platform) libvirtPlatform() (*asset.State, error) {
 
 	data, err := json.Marshal(platform)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrapf(err, "failed to Marshal %s platform", LibvirtPlatformType)
 	}
 
 	return &asset.State{
diff --git a/pkg/asset/installconfig/ssh.go b/pkg/asset/installconfig/ssh.go
index 73ef5d24ab8..13c2a31cd2b 100644
--- a/pkg/asset/installconfig/ssh.go
+++ b/pkg/asset/installconfig/ssh.go
@@ -1,7 +1,6 @@
 package installconfig
 
 import (
-	"errors"
 	"fmt"
 	"io/ioutil"
 	"os"
@@ -10,6 +9,7 @@ import (
 	"sort"
 	"strings"
 
+	"github.com/pkg/errors"
 	survey "gopkg.in/AlecAivazis/survey.v1"
 
 	"github.com/openshift/installer/pkg/asset"
@@ -45,7 +45,7 @@ func (a *sshPublicKey) Generate(map[asset.Asset]*asset.State) (state *asset.Stat
 	if value, ok := os.LookupEnv("OPENSHIFT_INSTALL_SSH_PUB_KEY"); ok {
 		if value != "" {
 			if err := validateOpenSSHPublicKey(value); err != nil {
-				return nil, err
+				return nil, errors.Wrap(err, "failed to validate public key")
 			}
 		}
 		return &asset.State{
@@ -59,7 +59,7 @@ func (a *sshPublicKey) Generate(map[asset.Asset]*asset.State) (state *asset.Stat
 	if path, ok := os.LookupEnv("OPENSHIFT_INSTALL_SSH_PUB_KEY_PATH"); ok {
 		key, err := readSSHKey(path)
 		if err != nil {
-			return nil, err
+			return nil, errors.Wrap(err, "failed to read public key file")
 		}
 		pubKeys[path] = key
 	} else {
@@ -68,7 +68,7 @@ func (a *sshPublicKey) Generate(map[asset.Asset]*asset.State) (state *asset.Stat
 		if home != "" {
 			paths, err := filepath.Glob(filepath.Join(home, ".ssh", "*.pub"))
 			if err != nil {
-				return nil, err
+				return nil, errors.Wrap(err, "failed to glob for public key files")
 			}
 			for _, path := range paths {
 				key, err := readSSHKey(path)
@@ -111,7 +111,7 @@ func (a *sshPublicKey) Generate(map[asset.Asset]*asset.State) (state *asset.Stat
 		return nil
 	})
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed UserInput for SSH public key")
 	}
 
 	return &asset.State{
diff --git a/pkg/asset/kubeconfig/kubeconfig.go b/pkg/asset/kubeconfig/kubeconfig.go
index 4e44a25ee26..be645290861 100644
--- a/pkg/asset/kubeconfig/kubeconfig.go
+++ b/pkg/asset/kubeconfig/kubeconfig.go
@@ -5,10 +5,12 @@ import (
 	"path/filepath"
 
 	"github.com/ghodss/yaml"
+	"github.com/pkg/errors"
+	clientcmd "k8s.io/client-go/tools/clientcmd/api/v1"
+
 	"github.com/openshift/installer/pkg/asset"
 	"github.com/openshift/installer/pkg/asset/installconfig"
 	"github.com/openshift/installer/pkg/asset/tls"
-	clientcmd "k8s.io/client-go/tools/clientcmd/api/v1"
 )
 
 const (
@@ -40,11 +42,9 @@ func (k *Kubeconfig) Dependencies() []asset.Asset {
 
 // Generate generates the kubeconfig.
 func (k *Kubeconfig) Generate(parents map[asset.Asset]*asset.State) (*asset.State, error) {
-	var err error
-
 	caCertData, err := asset.GetDataByFilename(k.rootCA, parents, tls.RootCACertName)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get RootCA from parents")
 	}
 
 	var keyFilename, certFilename, kubeconfigSuffix string
@@ -57,15 +57,15 @@ func (k *Kubeconfig) Generate(parents map[asset.Asset]*asset.State) (*asset.Stat
 	}
 	clientKeyData, err := asset.GetDataByFilename(k.certKey, parents, keyFilename)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get client certificate from parents")
 	}
 	clientCertData, err := asset.GetDataByFilename(k.certKey, parents, certFilename)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get client key from parents")
 	}
 	installConfig, err := installconfig.GetInstallConfig(k.installConfig, parents)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get InstallConfig from parents")
 	}
 
 	kubeconfig := clientcmd.Config{
@@ -101,7 +101,7 @@ func (k *Kubeconfig) Generate(parents map[asset.Asset]*asset.State) (*asset.Stat
 
 	data, err := yaml.Marshal(kubeconfig)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to Marshal kubeconfig")
 	}
 
 	return &asset.State{
diff --git a/pkg/asset/kubeconfig/kubeconfig_test.go b/pkg/asset/kubeconfig/kubeconfig_test.go
index e2b3afe9063..85bff2dddf9 100644
--- a/pkg/asset/kubeconfig/kubeconfig_test.go
+++ b/pkg/asset/kubeconfig/kubeconfig_test.go
@@ -153,7 +153,7 @@ users:
 				adminCertKey:  adminCertState,
 				installConfig: installConfigState,
 			},
-			errString:    "failed to find kubeconfig.fakeAsset in parents",
+			errString:    "failed to get RootCA from parents: failed to find kubeconfig.fakeAsset in parents",
 			expectedData: nil,
 		},
 		{
@@ -165,7 +165,7 @@ users:
 				kubeletCertKey: kubeletCertState,
 				installConfig:  installConfigState,
 			},
-			errString:    "failed to find kubeconfig.fakeAsset in parents",
+			errString:    "failed to get client certificate from parents: failed to find kubeconfig.fakeAsset in parents",
 			expectedData: nil,
 		},
 		{
@@ -177,7 +177,7 @@ users:
 				adminCertKey:  adminCertState,
 				installConfig: installConfigState,
 			},
-			errString:    "failed to find kubeconfig.fakeAsset in parents",
+			errString:    "failed to get client certificate from parents: failed to find kubeconfig.fakeAsset in parents",
 			expectedData: nil,
 		},
 		{
@@ -188,7 +188,7 @@ users:
 				rootCA:       rootCAState,
 				adminCertKey: adminCertState,
 			},
-			errString:    "failed to find kubeconfig.fakeAsset in parents",
+			errString:    "failed to get InstallConfig from parents: kubeconfig.fakeAsset does not exist in parents",
 			expectedData: nil,
 		},
 	}
diff --git a/pkg/asset/manifests/kube-addon-operator.go b/pkg/asset/manifests/kube-addon-operator.go
index 03282b3e645..684d421f209 100644
--- a/pkg/asset/manifests/kube-addon-operator.go
+++ b/pkg/asset/manifests/kube-addon-operator.go
@@ -4,6 +4,7 @@ import (
 	"fmt"
 
 	"github.com/ghodss/yaml"
+	"github.com/pkg/errors"
 
 	kubeaddon "github.com/coreos/tectonic-config/config/kube-addon"
 	"github.com/openshift/installer/pkg/asset"
@@ -38,14 +39,14 @@ func (kao *kubeAddonOperator) Dependencies() []asset.Asset {
 func (kao *kubeAddonOperator) Generate(dependencies map[asset.Asset]*asset.State) (*asset.State, error) {
 	ic, err := installconfig.GetInstallConfig(kao.installConfigAsset, dependencies)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get InstallConfig from parents")
 	}
 	kao.installConfig = ic
 
 	// installconfig is ready, we can create the addon config from it now
 	addonConfig, err := kao.addonConfig()
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrapf(err, "failed to create %s config from InstallConfig", kao.Name())
 	}
 
 	state := &asset.State{
diff --git a/pkg/asset/manifests/kube-core-operator.go b/pkg/asset/manifests/kube-core-operator.go
index ccaff3983b0..006cf38f32a 100644
--- a/pkg/asset/manifests/kube-core-operator.go
+++ b/pkg/asset/manifests/kube-core-operator.go
@@ -4,14 +4,15 @@ import (
 	"fmt"
 	"strings"
 
-	"github.com/ghodss/yaml"
-
 	"github.com/apparentlymart/go-cidr/cidr"
 	kubecore "github.com/coreos/tectonic-config/config/kube-core"
+	"github.com/ghodss/yaml"
+	"github.com/pkg/errors"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+
 	"github.com/openshift/installer/pkg/asset"
 	"github.com/openshift/installer/pkg/asset/installconfig"
 	"github.com/openshift/installer/pkg/types"
-	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 )
 
 const (
@@ -46,32 +47,28 @@ func (kco *kubeCoreOperator) Dependencies() []asset.Asset {
 func (kco *kubeCoreOperator) Generate(dependencies map[asset.Asset]*asset.State) (*asset.State, error) {
 	ic, err := installconfig.GetInstallConfig(kco.installConfigAsset, dependencies)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get InstallConfig from parents")
 	}
 	kco.installConfig = ic
 
 	// installconfig is ready, we can create the core config from it now
 	coreConfig, err := kco.coreConfig()
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrapf(err, "failed to create %s config from InstallConfig", kco.Name())
 	}
 
-	data, err := yaml.Marshal(coreConfig)
-	if err != nil {
-		return nil, fmt.Errorf("failed to marshal core config: %v", err)
-	}
 	state := &asset.State{
 		Contents: []asset.Content{
 			{
 				Name: "kco-config.yaml",
-				Data: data,
+				Data: coreConfig,
 			},
 		},
 	}
 	return state, nil
 }
 
-func (kco *kubeCoreOperator) coreConfig() (*kubecore.OperatorConfig, error) {
+func (kco *kubeCoreOperator) coreConfig() ([]byte, error) {
 	coreConfig := kubecore.OperatorConfig{
 		TypeMeta: metav1.TypeMeta{
 			APIVersion: kubecore.APIVersion,
@@ -99,8 +96,7 @@ func (kco *kubeCoreOperator) coreConfig() (*kubecore.OperatorConfig, error) {
 	coreConfig.NetworkConfig.ServiceCIDR = kco.installConfig.Networking.ServiceCIDR.String()
 	coreConfig.NetworkConfig.AdvertiseAddress = networkConfigAdvertiseAddress
 	coreConfig.NetworkConfig.EtcdServers = strings.Join(kco.getEtcdServersURLs(), ",")
-
-	return &coreConfig, nil
+	return yaml.Marshal(coreConfig)
 }
 
 func (kco *kubeCoreOperator) getAPIServerURL() string {
diff --git a/pkg/asset/manifests/machine-api-operator.go b/pkg/asset/manifests/machine-api-operator.go
index daf2a080eab..f839caef9ca 100644
--- a/pkg/asset/manifests/machine-api-operator.go
+++ b/pkg/asset/manifests/machine-api-operator.go
@@ -2,12 +2,12 @@ package manifests
 
 import (
 	"context"
-	"fmt"
 
 	"github.com/openshift/installer/pkg/asset"
 	"github.com/openshift/installer/pkg/asset/installconfig"
 	"github.com/openshift/installer/pkg/rhcos"
 	"github.com/openshift/installer/pkg/types"
+	"github.com/pkg/errors"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 )
 
@@ -80,14 +80,14 @@ func (mao *machineAPIOperator) Dependencies() []asset.Asset {
 func (mao *machineAPIOperator) Generate(dependencies map[asset.Asset]*asset.State) (*asset.State, error) {
 	ic, err := installconfig.GetInstallConfig(mao.installConfigAsset, dependencies)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get InstallConfig from parents")
 	}
 	mao.installConfig = ic
 
 	// installconfig is ready, we can create the mao config from it now
 	maoConfig, err := mao.maoConfig(dependencies)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrapf(err, "failed to create %s config from InstallConfig", mao.Name())
 	}
 
 	state := &asset.State{
@@ -120,7 +120,7 @@ func (mao *machineAPIOperator) maoConfig(dependencies map[asset.Asset]*asset.Sta
 
 		ami, err := rhcos.AMI(context.TODO(), DefaultChannel, mao.installConfig.Platform.AWS.Region)
 		if err != nil {
-			return "", fmt.Errorf("failed to lookup RHCOS AMI: %v", err)
+			return "", errors.Wrapf(err, "failed to get AMI for %s config", mao.Name())
 		}
 
 		cfg.AWS = &awsConfig{
@@ -147,7 +147,7 @@ func (mao *machineAPIOperator) maoConfig(dependencies map[asset.Asset]*asset.Sta
 			Replicas:    int(*mao.installConfig.Machines[1].Replicas),
 		}
 	} else {
-		return "", fmt.Errorf("unknown provider for machine-api-operator")
+		return "", errors.Errorf("unknown provider for machine-api-operator")
 	}
 
 	return marshalYAML(cfg)
diff --git a/pkg/asset/manifests/network-operator.go b/pkg/asset/manifests/network-operator.go
index ee7cd0e8f24..e0297cf99be 100644
--- a/pkg/asset/manifests/network-operator.go
+++ b/pkg/asset/manifests/network-operator.go
@@ -2,6 +2,7 @@ package manifests
 
 import (
 	"github.com/ghodss/yaml"
+	"github.com/pkg/errors"
 
 	"github.com/openshift/installer/pkg/asset"
 	"github.com/openshift/installer/pkg/asset/installconfig"
@@ -40,19 +41,19 @@ func (no *networkOperator) Dependencies() []asset.Asset {
 func (no *networkOperator) Generate(dependencies map[asset.Asset]*asset.State) (*asset.State, error) {
 	ic, err := installconfig.GetInstallConfig(no.installConfigAsset, dependencies)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get InstallConfig from parents")
 	}
 	no.installConfig = ic
 
 	// installconfig is ready, we can create the core config from it now
 	netConfig, err := no.netConfig()
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrapf(err, "failed to create %s config from InstallConfig", no.Name())
 	}
 
 	netManifest, err := no.manifest()
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrapf(err, "failed to create %s manifests from InstallConfig", no.Name())
 	}
 	state := &asset.State{
 		Contents: []asset.Content{
diff --git a/pkg/asset/manifests/operators.go b/pkg/asset/manifests/operators.go
index 138552efc21..5064658e15e 100644
--- a/pkg/asset/manifests/operators.go
+++ b/pkg/asset/manifests/operators.go
@@ -7,6 +7,8 @@ import (
 	"path/filepath"
 	"text/template"
 
+	"github.com/pkg/errors"
+
 	"github.com/openshift/installer/pkg/asset"
 	"github.com/openshift/installer/pkg/asset/installconfig"
 	"github.com/openshift/installer/pkg/asset/manifests/content/bootkube"
@@ -95,7 +97,7 @@ func (m *manifests) Generate(dependencies map[asset.Asset]*asset.State) (*asset.
 		"mao-config":     string(mao.Data),
 	})
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to create kube-system/cluster-config-v1 configmap")
 	}
 
 	// addon goes to openshift system
@@ -103,7 +105,7 @@ func (m *manifests) Generate(dependencies map[asset.Asset]*asset.State) (*asset.
 		"addon-config": string(addon.Data),
 	})
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to create tectonic-system/cluster-config-v1 configmap")
 	}
 
 	state := &asset.State{
diff --git a/pkg/asset/manifests/tectonic.go b/pkg/asset/manifests/tectonic.go
index bfe5778a3b4..c8d4e5bc9d4 100644
--- a/pkg/asset/manifests/tectonic.go
+++ b/pkg/asset/manifests/tectonic.go
@@ -5,6 +5,8 @@ import (
 	"encoding/base64"
 	"path/filepath"
 
+	"github.com/pkg/errors"
+
 	"github.com/openshift/installer/pkg/asset"
 	"github.com/openshift/installer/pkg/asset/installconfig"
 	content "github.com/openshift/installer/pkg/asset/manifests/content/tectonic"
@@ -38,7 +40,7 @@ func (t *tectonic) Dependencies() []asset.Asset {
 func (t *tectonic) Generate(dependencies map[asset.Asset]*asset.State) (*asset.State, error) {
 	ic, err := installconfig.GetInstallConfig(t.installConfig, dependencies)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get InstallConfig from parents")
 	}
 	ingressContents := dependencies[t.ingressCertKey].Contents
 	templateData := &tectonicTemplateData{
diff --git a/pkg/asset/metadata/metadata.go b/pkg/asset/metadata/metadata.go
index 14cbaeb54be..115d63c24ab 100644
--- a/pkg/asset/metadata/metadata.go
+++ b/pkg/asset/metadata/metadata.go
@@ -4,6 +4,8 @@ import (
 	"encoding/json"
 	"fmt"
 
+	"github.com/pkg/errors"
+
 	"github.com/openshift/installer/pkg/asset"
 	"github.com/openshift/installer/pkg/asset/installconfig"
 	"github.com/openshift/installer/pkg/types"
@@ -37,7 +39,7 @@ func (m *Metadata) Dependencies() []asset.Asset {
 func (m *Metadata) Generate(parents map[asset.Asset]*asset.State) (*asset.State, error) {
 	installCfg, err := installconfig.GetInstallConfig(m.installConfig, parents)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get InstallConfig from parents")
 	}
 
 	cm := &types.ClusterMetadata{
@@ -68,7 +70,7 @@ func (m *Metadata) Generate(parents map[asset.Asset]*asset.State) (*asset.State,
 
 	data, err := json.Marshal(cm)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to Marshal ClusterMetadata")
 	}
 	return &asset.State{
 		Contents: []asset.Content{
diff --git a/pkg/asset/state.go b/pkg/asset/state.go
index f94c9cb4762..bd92151627c 100644
--- a/pkg/asset/state.go
+++ b/pkg/asset/state.go
@@ -4,6 +4,8 @@ import (
 	"io/ioutil"
 	"os"
 	"path/filepath"
+
+	"github.com/pkg/errors"
 )
 
 // State is the state of an Asset.
@@ -20,16 +22,20 @@ type Content struct {
 // PersistToFile persists the data in the State to files. Each Content entry that
 // has a non-empty Name will be persisted to a file with that name.
 func (s *State) PersistToFile(directory string) error {
+	if s == nil {
+		return nil
+	}
+
 	for _, c := range s.Contents {
 		if c.Name == "" {
 			continue
 		}
 		path := filepath.Join(directory, c.Name)
 		if err := os.MkdirAll(filepath.Dir(path), 0755); err != nil {
-			return err
+			return errors.Wrap(err, "failed to create dir")
 		}
 		if err := ioutil.WriteFile(path, c.Data, 0644); err != nil {
-			return err
+			return errors.Wrap(err, "failed to write file")
 		}
 	}
 	return nil
diff --git a/pkg/asset/store.go b/pkg/asset/store.go
index 0137ed1f520..eaf159306e2 100644
--- a/pkg/asset/store.go
+++ b/pkg/asset/store.go
@@ -1,8 +1,7 @@
 package asset
 
 import (
-	"fmt"
-
+	"github.com/pkg/errors"
 	"github.com/sirupsen/logrus"
 )
 
@@ -40,7 +39,7 @@ func (s *StoreImpl) fetch(asset Asset, indent string) (*State, error) {
 	for _, d := range dependencies {
 		ds, err := s.fetch(d, indent+"  ")
 		if err != nil {
-			return nil, err
+			return nil, errors.Wrapf(err, "failed to fetch dependency for %s", asset.Name())
 		}
 		dependenciesStates[d] = ds
 	}
@@ -48,7 +47,7 @@ func (s *StoreImpl) fetch(asset Asset, indent string) (*State, error) {
 	logrus.Debugf("%sGenerating %s...", indent, asset.Name())
 	state, err := asset.Generate(dependenciesStates)
 	if err != nil {
-		return nil, fmt.Errorf("failed to generate asset %q: %v", asset.Name(), err)
+		return nil, errors.Wrapf(err, "failed to generate asset %s", asset.Name())
 	}
 	if s.assets == nil {
 		s.assets = make(map[Asset]*State)
diff --git a/pkg/asset/tls/certkey.go b/pkg/asset/tls/certkey.go
index bd83a77acf3..58e0ff14124 100644
--- a/pkg/asset/tls/certkey.go
+++ b/pkg/asset/tls/certkey.go
@@ -9,9 +9,10 @@ import (
 	"path/filepath"
 	"time"
 
-	"github.com/ghodss/yaml"
 	"github.com/openshift/installer/pkg/asset"
+	"github.com/openshift/installer/pkg/asset/installconfig"
 	"github.com/openshift/installer/pkg/types"
+	"github.com/pkg/errors"
 )
 
 const (
@@ -74,33 +75,27 @@ func (c *CertKey) Generate(parents map[asset.Asset]*asset.State) (*asset.State,
 	}
 
 	if c.GenSubject != nil || c.GenDNSNames != nil || c.GenIPAddresses != nil {
-		state, ok := parents[c.installConfig]
-		if !ok {
-			return nil, fmt.Errorf("failed to get install config state in the parent asset states")
+		installConfig, err := installconfig.GetInstallConfig(c.installConfig, parents)
+		if err != nil {
+			return nil, errors.Wrap(err, "failed to get InstallConfig from parents")
 		}
 
-		var installConfig types.InstallConfig
-		if err := yaml.Unmarshal(state.Contents[0].Data, &installConfig); err != nil {
-			return nil, fmt.Errorf("failed to unmarshal install config: %v", err)
-		}
-
-		var err error
 		if c.GenSubject != nil {
-			cfg.Subject, err = c.GenSubject(&installConfig)
+			cfg.Subject, err = c.GenSubject(installConfig)
 			if err != nil {
-				return nil, fmt.Errorf("failed to generate Subject: %v", err)
+				return nil, errors.Wrap(err, "failed to generate Subject")
 			}
 		}
 		if c.GenDNSNames != nil {
-			cfg.DNSNames, err = c.GenDNSNames(&installConfig)
+			cfg.DNSNames, err = c.GenDNSNames(installConfig)
 			if err != nil {
-				return nil, fmt.Errorf("failed to generate DNSNames: %v", err)
+				return nil, errors.Wrap(err, "failed to generate DNSNames")
 			}
 		}
 		if c.GenIPAddresses != nil {
-			cfg.IPAddresses, err = c.GenIPAddresses(&installConfig)
+			cfg.IPAddresses, err = c.GenIPAddresses(installConfig)
 			if err != nil {
-				return nil, fmt.Errorf("failed to generate IPAddresses: %v", err)
+				return nil, errors.Wrap(err, "failed to generate IPAddresses")
 			}
 		}
 	}
@@ -111,17 +106,17 @@ func (c *CertKey) Generate(parents map[asset.Asset]*asset.State) (*asset.State,
 
 	state, ok := parents[c.ParentCA]
 	if !ok {
-		return nil, fmt.Errorf("failed to get parent CA %v in the parent asset states", c.ParentCA)
+		return nil, errors.Errorf("failed to get parent CA %v in the parent asset states", c.ParentCA)
 	}
 
 	caKey, caCert, err := parseCAFromAssetState(state)
 	if err != nil {
-		return nil, fmt.Errorf("failed to parse CA from asset: %v", err)
+		return nil, errors.Wrap(err, "failed to parse CA from asset")
 	}
 
 	key, crt, err = GenerateCert(caKey, caCert, cfg)
 	if err != nil {
-		return nil, fmt.Errorf("failed to generate cert/key pair: %v", err)
+		return nil, errors.Wrap(err, "failed to generate cert/key pair")
 	}
 
 	keyData := []byte(PrivateKeyToPem(key))
@@ -156,7 +151,7 @@ func parseCAFromAssetState(ca *asset.State) (*rsa.PrivateKey, *x509.Certificate,
 	var err error
 
 	if len(ca.Contents) != 2 {
-		return nil, nil, fmt.Errorf("expect key and cert in the contents of CA, got: %v", ca)
+		return nil, nil, errors.Errorf("expected key and cert in the contents of CA, got: %v", ca)
 	}
 
 	for _, c := range ca.Contents {
@@ -164,15 +159,15 @@ func parseCAFromAssetState(ca *asset.State) (*rsa.PrivateKey, *x509.Certificate,
 		case ".key":
 			key, err = PemToPrivateKey(c.Data)
 			if err != nil {
-				return nil, nil, fmt.Errorf("failed to parse rsa private key: %v", err)
+				return nil, nil, errors.Wrap(err, "failed to parse rsa private key")
 			}
 		case ".crt":
 			cert, err = PemToCertificate(c.Data)
 			if err != nil {
-				return nil, nil, fmt.Errorf("failed to parse x509 certificate: %v", err)
+				return nil, nil, errors.Wrap(err, "failed to parse x509 certificate")
 			}
 		default:
-			return nil, nil, fmt.Errorf("unexpected content name: %v", c.Name)
+			return nil, nil, errors.Errorf("unexpected content name: %v", c.Name)
 		}
 	}
 
diff --git a/pkg/asset/tls/certkey_test.go b/pkg/asset/tls/certkey_test.go
index 68d26714dfd..b68c59c8deb 100644
--- a/pkg/asset/tls/certkey_test.go
+++ b/pkg/asset/tls/certkey_test.go
@@ -118,7 +118,7 @@ func TestCertKeyGenerate(t *testing.T) {
 				GenDNSNames:    testGenDNSNames,
 				GenIPAddresses: testGenIPAddresses,
 			},
-			errString: "failed to get install config state in the parent asset states",
+			errString: "failed to get InstallConfig from parents: tls.fakeInstallConfig does not exist in parents",
 			parents:   nil,
 		},
 	}
diff --git a/pkg/asset/tls/keypair.go b/pkg/asset/tls/keypair.go
index 6f485df84ae..40ea9351ef0 100644
--- a/pkg/asset/tls/keypair.go
+++ b/pkg/asset/tls/keypair.go
@@ -4,6 +4,7 @@ import (
 	"fmt"
 
 	"github.com/openshift/installer/pkg/asset"
+	"github.com/pkg/errors"
 )
 
 // KeyPair implements the Asset interface and
@@ -24,12 +25,12 @@ func (k *KeyPair) Dependencies() []asset.Asset {
 func (k *KeyPair) Generate(map[asset.Asset]*asset.State) (*asset.State, error) {
 	key, err := PrivateKey()
 	if err != nil {
-		return nil, fmt.Errorf("failed to generate private key: %v", err)
+		return nil, errors.Wrap(err, "failed to generate private key")
 	}
 
 	pubkeyData, err := PublicKeyToPem(&key.PublicKey)
 	if err != nil {
-		return nil, fmt.Errorf("failed to get public key data: %v", err)
+		return nil, errors.Wrap(err, "failed to get public key data from private key")
 	}
 
 	return &asset.State{
diff --git a/pkg/asset/tls/root.go b/pkg/asset/tls/root.go
index 67df4c5540e..29696745f42 100644
--- a/pkg/asset/tls/root.go
+++ b/pkg/asset/tls/root.go
@@ -3,9 +3,9 @@ package tls
 import (
 	"crypto/x509"
 	"crypto/x509/pkix"
-	"fmt"
 
 	"github.com/openshift/installer/pkg/asset"
+	"github.com/pkg/errors"
 )
 
 // RootCA contains the private key and the cert that's
@@ -30,7 +30,7 @@ func (c *RootCA) Generate(parents map[asset.Asset]*asset.State) (*asset.State, e
 
 	key, crt, err := GenerateRootCertKey(cfg)
 	if err != nil {
-		return nil, fmt.Errorf("failed to generate RootCA %v", err)
+		return nil, errors.Wrap(err, "failed to generate RootCA")
 	}
 
 	return &asset.State{
diff --git a/pkg/asset/tls/tls.go b/pkg/asset/tls/tls.go
index 7990a6545d3..75957f38559 100644
--- a/pkg/asset/tls/tls.go
+++ b/pkg/asset/tls/tls.go
@@ -10,12 +10,12 @@ import (
 	"crypto/x509"
 	"crypto/x509/pkix"
 	"encoding/asn1"
-	"errors"
-	"fmt"
 	"math"
 	"math/big"
 	"net"
 	"time"
+
+	"github.com/pkg/errors"
 )
 
 const (
@@ -50,7 +50,7 @@ type rsaPublicKey struct {
 func PrivateKey() (*rsa.PrivateKey, error) {
 	rsaKey, err := rsa.GenerateKey(rand.Reader, keySize)
 	if err != nil {
-		return nil, fmt.Errorf("error generating RSA private key: %v", err)
+		return nil, errors.Wrap(err, "error generating RSA private key")
 	}
 
 	return rsaKey, nil
@@ -71,16 +71,16 @@ func SelfSignedCACert(cfg *CertCfg, key *rsa.PrivateKey) (*x509.Certificate, err
 	}
 	// verifies that the CN and/or OU for the cert is set
 	if len(cfg.Subject.CommonName) == 0 || len(cfg.Subject.OrganizationalUnit) == 0 {
-		return nil, fmt.Errorf("certification's subject is not set, or invalid")
+		return nil, errors.Errorf("certification's subject is not set, or invalid")
 	}
 	pub := key.Public()
 	cert.SubjectKeyId, err = generateSubjectKeyID(pub)
 	if err != nil {
-		return nil, fmt.Errorf("failed to set subject key identifier: %v", err)
+		return nil, errors.Wrap(err, "failed to set subject key identifier")
 	}
 	certBytes, err := x509.CreateCertificate(rand.Reader, &cert, &cert, key.Public(), key)
 	if err != nil {
-		return nil, fmt.Errorf("error creating certificate: %v", err)
+		return nil, errors.Wrap(err, "failed to create certificate")
 	}
 	return x509.ParseCertificate(certBytes)
 }
@@ -114,11 +114,11 @@ func SignedCertificate(
 	pub := caCert.PublicKey.(*rsa.PublicKey)
 	certTmpl.SubjectKeyId, err = generateSubjectKeyID(pub)
 	if err != nil {
-		return nil, fmt.Errorf("failed to set subject key identifier: %v", err)
+		return nil, errors.Wrap(err, "failed to set subject key identifier")
 	}
 	certBytes, err := x509.CreateCertificate(rand.Reader, &certTmpl, caCert, key.Public(), caKey)
 	if err != nil {
-		return nil, fmt.Errorf("error creating signed certificate: %v", err)
+		return nil, errors.Wrap(err, "failed to create x509 certificate")
 	}
 	return x509.ParseCertificate(certBytes)
 }
@@ -132,7 +132,7 @@ func generateSubjectKeyID(pub crypto.PublicKey) ([]byte, error) {
 	case *rsa.PublicKey:
 		publicKeyBytes, err = asn1.Marshal(rsaPublicKey{N: pub.N, E: pub.E})
 		if err != nil {
-			return nil, err
+			return nil, errors.Wrap(err, "failed to Marshal ans1 public key")
 		}
 	case *ecdsa.PublicKey:
 		publicKeyBytes = elliptic.Marshal(pub.Curve, pub.X, pub.Y)
@@ -154,24 +154,24 @@ func GenerateCert(caKey *rsa.PrivateKey,
 	// create a private key
 	key, err := PrivateKey()
 	if err != nil {
-		return nil, nil, fmt.Errorf("failed to generate private key: %v", err)
+		return nil, nil, errors.Wrap(err, "failed to generate private key")
 	}
 
 	// create a CSR
 	csrTmpl := x509.CertificateRequest{Subject: cfg.Subject, DNSNames: cfg.DNSNames, IPAddresses: cfg.IPAddresses}
 	csrBytes, err := x509.CreateCertificateRequest(rand.Reader, &csrTmpl, key)
 	if err != nil {
-		return nil, nil, fmt.Errorf("error creating certificate request: %v", err)
+		return nil, nil, errors.Wrap(err, "failed to create certificate request")
 	}
 	csr, err := x509.ParseCertificateRequest(csrBytes)
 	if err != nil {
-		return nil, nil, fmt.Errorf("error parsing certificate request: %v", err)
+		return nil, nil, errors.Wrap(err, "error parsing x509 certificate request")
 	}
 
 	// create a cert
 	cert, err := GenerateSignedCert(cfg, csr, key, caKey, caCert)
 	if err != nil {
-		return nil, nil, fmt.Errorf("failed to create a certificate: %v", err)
+		return nil, nil, errors.Wrap(err, "failed to create a signed certificate")
 	}
 	return key, cert, nil
 }
@@ -180,7 +180,7 @@ func GenerateCert(caKey *rsa.PrivateKey,
 func GenerateRootCA(key *rsa.PrivateKey, cfg *CertCfg) (*x509.Certificate, error) {
 	cert, err := SelfSignedCACert(cfg, key)
 	if err != nil {
-		return nil, fmt.Errorf("error generating self signed certificate: %v", err)
+		return nil, errors.Wrap(err, "failed to generate self signed certificate")
 	}
 	return cert, nil
 }
@@ -193,7 +193,7 @@ func GenerateSignedCert(cfg *CertCfg,
 	caCert *x509.Certificate) (*x509.Certificate, error) {
 	cert, err := SignedCertificate(cfg, csr, key, caCert, caKey)
 	if err != nil {
-		return nil, fmt.Errorf("error signing certificate: %v", err)
+		return nil, errors.Wrap(err, "failed to create a signed certificate")
 	}
 	return cert, nil
 }
@@ -202,13 +202,12 @@ func GenerateSignedCert(cfg *CertCfg,
 func GenerateRootCertKey(cfg *CertCfg) (*rsa.PrivateKey, *x509.Certificate, error) {
 	key, err := PrivateKey()
 	if err != nil {
-		return nil, nil, fmt.Errorf("failed to generate private key: %v", err)
+		return nil, nil, errors.Wrap(err, "failed to generate private key")
 	}
 
 	crt, err := GenerateRootCA(key, cfg)
 	if err != nil {
-		return nil, nil, fmt.Errorf("failed to create a certificate: %v", err)
+		return nil, nil, errors.Wrap(err, "failed to create root CA certificate")
 	}
-
 	return key, crt, nil
 }
diff --git a/pkg/asset/tls/utils.go b/pkg/asset/tls/utils.go
index e972476d12e..c0414d8e90a 100644
--- a/pkg/asset/tls/utils.go
+++ b/pkg/asset/tls/utils.go
@@ -4,6 +4,8 @@ import (
 	"crypto/rsa"
 	"crypto/x509"
 	"encoding/pem"
+
+	"github.com/pkg/errors"
 )
 
 // PrivateKeyToPem converts an rsa.PrivateKey object to pem string
@@ -44,7 +46,7 @@ func CSRToPem(cert *x509.CertificateRequest) string {
 func PublicKeyToPem(key *rsa.PublicKey) (string, error) {
 	keyInBytes, err := x509.MarshalPKIXPublicKey(key)
 	if err != nil {
-		return "", err
+		return "", errors.Wrap(err, "failed to MarshalPKIXPublicKey")
 	}
 	keyinPem := pem.EncodeToMemory(
 		&pem.Block{
diff --git a/pkg/asset/userprovided.go b/pkg/asset/userprovided.go
index 611dba2df03..c6093e2ffb5 100644
--- a/pkg/asset/userprovided.go
+++ b/pkg/asset/userprovided.go
@@ -4,6 +4,7 @@ import (
 	"io/ioutil"
 	"os"
 
+	"github.com/pkg/errors"
 	survey "gopkg.in/AlecAivazis/survey.v1"
 )
 
@@ -23,7 +24,13 @@ func (a *UserProvided) Dependencies() []Asset {
 }
 
 // Generate queries for input from the user.
-func (a *UserProvided) Generate(map[Asset]*State) (*State, error) {
+func (a *UserProvided) Generate(map[Asset]*State) (state *State, err error) {
+	defer func() {
+		if err != nil {
+			err = errors.Wrapf(err, "failed to acquire user-provided input %s", a.AssetName)
+		}
+	}()
+
 	var response string
 
 	if value, ok := os.LookupEnv(a.EnvVarName); ok {
@@ -31,18 +38,18 @@ func (a *UserProvided) Generate(map[Asset]*State) (*State, error) {
 	} else if path, ok := os.LookupEnv(a.PathEnvVarName); ok {
 		value, err := ioutil.ReadFile(path)
 		if err != nil {
-			return nil, err
+			return nil, errors.Wrapf(err, "failed to read file from %s", a.PathEnvVarName)
 		}
 		response = string(value)
 	}
 
 	if response == "" {
 		if err := survey.Ask([]*survey.Question{a.Question}, &response); err != nil {
-			return nil, err
+			return nil, errors.Wrap(err, "failed to Ask")
 		}
 	} else if a.Question.Validate != nil {
 		if err := a.Question.Validate(response); err != nil {
-			return nil, err
+			return nil, errors.Wrap(err, "validation failed")
 		}
 	}
 
diff --git a/pkg/destroy/destroyer.go b/pkg/destroy/destroyer.go
index 20e0493ecec..00e82badbf4 100644
--- a/pkg/destroy/destroyer.go
+++ b/pkg/destroy/destroyer.go
@@ -2,10 +2,10 @@ package destroy
 
 import (
 	"encoding/json"
-	"fmt"
 	"io/ioutil"
 	"path/filepath"
 
+	"github.com/pkg/errors"
 	"github.com/sirupsen/logrus"
 
 	"github.com/openshift/installer/pkg/asset/metadata"
@@ -29,22 +29,22 @@ func New(logger logrus.FieldLogger, rootDir string) (Destroyer, error) {
 	path := filepath.Join(rootDir, metadata.MetadataFilename)
 	raw, err := ioutil.ReadFile(filepath.Join(rootDir, metadata.MetadataFilename))
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrapf(err, "failed to read %s file", metadata.MetadataFilename)
 	}
 
 	var cmetadata *types.ClusterMetadata
 	if err := json.Unmarshal(raw, &cmetadata); err != nil {
-		return nil, err
+		return nil, errors.Wrapf(err, "failed to Unmarshal data from %s file to types.ClusterMetadata", metadata.MetadataFilename)
 	}
 
 	platform := cmetadata.Platform()
 	if platform == "" {
-		return nil, fmt.Errorf("no platform configured in %q", path)
+		return nil, errors.Errorf("no platform configured in %q", path)
 	}
 
 	creator, ok := Registry[platform]
 	if !ok {
-		return nil, fmt.Errorf("no destroyers registered for %q", platform)
+		return nil, errors.Errorf("no destroyers registered for %q", platform)
 	}
 	return creator(logger, cmetadata)
 }
diff --git a/pkg/destroy/libvirt/libvirt_prefix_deprovision.go b/pkg/destroy/libvirt/libvirt_prefix_deprovision.go
index 3891fbc7889..3ebf6b1e692 100644
--- a/pkg/destroy/libvirt/libvirt_prefix_deprovision.go
+++ b/pkg/destroy/libvirt/libvirt_prefix_deprovision.go
@@ -8,10 +8,12 @@ import (
 	"time"
 
 	libvirt "github.com/libvirt/libvirt-go"
-	"github.com/openshift/installer/pkg/destroy"
-	"github.com/openshift/installer/pkg/types"
+	"github.com/pkg/errors"
 	"github.com/sirupsen/logrus"
 	"k8s.io/apimachinery/pkg/util/wait"
+
+	"github.com/openshift/installer/pkg/destroy"
+	"github.com/openshift/installer/pkg/types"
 )
 
 // filterFunc allows filtering based on names.
@@ -61,7 +63,7 @@ func (o *ClusterUninstaller) Run() error {
 
 	conn, err := libvirt.NewConnect(o.LibvirtURI)
 	if err != nil {
-		return err
+		return errors.Wrap(err, "failed to connect to Libvirt daemon")
 	}
 
 	// launch goroutines
diff --git a/pkg/ipnet/ipnet.go b/pkg/ipnet/ipnet.go
index 59c20d976a6..eff16ee0c8f 100644
--- a/pkg/ipnet/ipnet.go
+++ b/pkg/ipnet/ipnet.go
@@ -5,6 +5,8 @@ import (
 	"encoding/json"
 	"net"
 	"reflect"
+
+	"github.com/pkg/errors"
 )
 
 var nullString = "null"
@@ -45,12 +47,12 @@ func (ipnet *IPNet) UnmarshalJSON(b []byte) (err error) {
 	var cidr string
 	err = json.Unmarshal(b, &cidr)
 	if err != nil {
-		return err
+		return errors.Wrap(err, "failed to Unmarshal string")
 	}
 
 	ip, net, err := net.ParseCIDR(cidr)
 	if err != nil {
-		return err
+		return errors.Wrap(err, "failed to Parse cidr string to net.IPNet")
 	}
 
 	// This check is needed in order to work around a strange quirk in the Go
diff --git a/pkg/rhcos/ami.go b/pkg/rhcos/ami.go
index ba382769d60..462d59026d1 100644
--- a/pkg/rhcos/ami.go
+++ b/pkg/rhcos/ami.go
@@ -2,12 +2,12 @@ package rhcos
 
 import (
 	"context"
-	"fmt"
 	"time"
 
 	"github.com/aws/aws-sdk-go/aws"
 	"github.com/aws/aws-sdk-go/aws/session"
 	"github.com/aws/aws-sdk-go/service/ec2"
+	"github.com/pkg/errors"
 )
 
 const (
@@ -18,7 +18,7 @@ const (
 // AMI calculates a Red Hat CoreOS AMI.
 func AMI(ctx context.Context, channel, region string) (ami string, err error) {
 	if channel != DefaultChannel {
-		return "", fmt.Errorf("channel %q is not yet supported", channel)
+		return "", errors.Errorf("channel %q is not yet supported", channel)
 	}
 
 	ssn := session.Must(session.NewSessionWithOptions(session.Options{
@@ -59,7 +59,7 @@ func AMI(ctx context.Context, channel, region string) (ami string, err error) {
 		},
 	})
 	if err != nil {
-		return "", err
+		return "", errors.Wrap(err, "failed to describe AMIs")
 	}
 
 	var image *ec2.Image
@@ -70,7 +70,7 @@ func AMI(ctx context.Context, channel, region string) (ami string, err error) {
 		}
 		nextCreated, err := time.Parse(time.RFC3339, *nextImage.CreationDate)
 		if err != nil {
-			return "", err
+			return "", errors.Wrap(err, "failed to parse AMIs CreationDate to time.RFC3339")
 		}
 
 		if image == nil || nextCreated.After(created) {
@@ -80,7 +80,7 @@ func AMI(ctx context.Context, channel, region string) (ami string, err error) {
 	}
 
 	if image == nil {
-		return "", fmt.Errorf("no RHCOS AMIs found in %s", region)
+		return "", errors.Errorf("no RHCOS AMIs found in %s", region)
 	}
 
 	return *image.ImageId, nil
diff --git a/pkg/terraform/executor.go b/pkg/terraform/executor.go
index 3c526b8101c..d55b4afb182 100644
--- a/pkg/terraform/executor.go
+++ b/pkg/terraform/executor.go
@@ -1,13 +1,12 @@
 package terraform
 
 import (
-	"errors"
-	"fmt"
 	"os"
 	"os/exec"
 	"path/filepath"
 	"runtime"
 
+	"github.com/pkg/errors"
 	"github.com/sirupsen/logrus"
 )
 
@@ -40,7 +39,7 @@ func newExecutor() (*executor, error) {
 	// Find the Terraform binary.
 	binPath, err := tfBinaryPath()
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to get Terraform binary's path")
 	}
 
 	ex.binaryPath = binPath
@@ -56,7 +55,7 @@ func (ex *executor) execute(clusterDir string, args ...string) error {
 	// Prepare Terraform command by setting up the command, configuration,
 	// and the working directory
 	if clusterDir == "" {
-		return fmt.Errorf("clusterDir is unset. Quitting")
+		return errors.Errorf("clusterDir is unset. Quitting")
 	}
 
 	cmd := exec.Command(ex.binaryPath, args...)
diff --git a/pkg/terraform/terraform.go b/pkg/terraform/terraform.go
index 9bdd1171afb..3b39f8a73f3 100644
--- a/pkg/terraform/terraform.go
+++ b/pkg/terraform/terraform.go
@@ -3,18 +3,20 @@ package terraform
 import (
 	"fmt"
 	"path"
+
+	"github.com/pkg/errors"
 )
 
 func terraformExec(clusterDir string, args ...string) error {
 	// Create an executor
 	ex, err := newExecutor()
 	if err != nil {
-		return fmt.Errorf("could not create Terraform executor: %s", err)
+		return errors.Wrap(err, "failed to create Terraform executor")
 	}
 
 	err = ex.execute(clusterDir, args...)
 	if err != nil {
-		return fmt.Errorf("failed to run Terraform: %s", err)
+		return errors.Wrap(err, "failed to execute Terraform")
 	}
 	return nil
 }
diff --git a/pkg/types/config/cluster.go b/pkg/types/config/cluster.go
index 10b6d4e15b3..70c42d50dd7 100644
--- a/pkg/types/config/cluster.go
+++ b/pkg/types/config/cluster.go
@@ -3,10 +3,10 @@ package config
 import (
 	"context"
 	"encoding/json"
-	"fmt"
 	"time"
 
 	"github.com/coreos/tectonic-config/config/tectonic-network"
+	"github.com/pkg/errors"
 	"gopkg.in/yaml.v2"
 
 	"github.com/openshift/installer/pkg/rhcos"
@@ -39,7 +39,7 @@ func (p *Platform) UnmarshalYAML(unmarshal func(interface{}) error) error {
 	switch platform {
 	case PlatformAWS, PlatformLibvirt, PlatformOpenStack:
 	default:
-		return fmt.Errorf("invalid platform specified (%s); must be one of %s", platform, []Platform{PlatformAWS, PlatformLibvirt, PlatformOpenStack})
+		return errors.Errorf("invalid platform specified (%s); must be one of %s", platform, []Platform{PlatformAWS, PlatformLibvirt, PlatformOpenStack})
 	}
 
 	*p = platform
@@ -116,13 +116,13 @@ func (c *Cluster) TFVars() (string, error) {
 	// Fill in master ips
 	if c.Platform == PlatformLibvirt {
 		if err := c.Libvirt.TFVars(c.Master.Count, c.Worker.Count); err != nil {
-			return "", err
+			return "", errors.Wrap(err, "failed to create TFVars for libvirt platfrom")
 		}
 	}
 
 	data, err := json.MarshalIndent(&c, "", "  ")
 	if err != nil {
-		return "", err
+		return "", errors.Wrap(err, "failed to marshal TFVars")
 	}
 
 	return string(data), nil
@@ -144,7 +144,7 @@ func (c *Cluster) YAML() (string, error) {
 
 	yaml, err := yaml.Marshal(c)
 	if err != nil {
-		return "", err
+		return "", errors.Wrap(err, "failed to marshal config.Cluster")
 	}
 
 	return string(yaml), nil
@@ -186,7 +186,7 @@ func ConvertInstallConfigToTFVars(cfg *types.InstallConfig, bootstrapIgn string,
 		defer cancel()
 		ami, err := rhcos.AMI(ctx, rhcos.DefaultChannel, cfg.Platform.AWS.Region)
 		if err != nil {
-			return nil, fmt.Errorf("failed to determine default AMI: %v", err)
+			return nil, errors.Wrap(err, "failed to determine default AMI")
 		}
 
 		cluster.Platform = PlatformAWS
@@ -268,14 +268,14 @@ func ConvertInstallConfigToTFVars(cfg *types.InstallConfig, bootstrapIgn string,
 				}
 			}
 		default:
-			return nil, fmt.Errorf("unrecognized machine pool %q", m.Name)
+			return nil, errors.Errorf("unrecognized machine pool %q", m.Name)
 		}
 
 	}
 
 	// Validate the TFVars.
 	if err := cluster.ValidateAndLog(); err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to validate TFVars")
 	}
 
 	return cluster, nil
diff --git a/pkg/types/config/parser.go b/pkg/types/config/parser.go
index 050b9c94485..cb8116b0970 100644
--- a/pkg/types/config/parser.go
+++ b/pkg/types/config/parser.go
@@ -2,11 +2,10 @@ package config
 
 import (
 	"context"
-	"errors"
-	"fmt"
 	"io/ioutil"
 	"time"
 
+	"github.com/pkg/errors"
 	"gopkg.in/yaml.v2"
 
 	"github.com/openshift/installer/pkg/rhcos"
@@ -17,7 +16,7 @@ func ParseConfig(data []byte) (*Cluster, error) {
 	cluster := defaultCluster
 
 	if err := yaml.Unmarshal(data, &cluster); err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to unmarshal to config.Cluster")
 	}
 
 	// Deprecated: remove after openshift/release is ported to pullSecret
@@ -28,7 +27,7 @@ func ParseConfig(data []byte) (*Cluster, error) {
 
 		data, err := ioutil.ReadFile(cluster.PullSecretPath)
 		if err != nil {
-			return nil, err
+			return nil, errors.Wrap(err, "failed to read PullSecretPath")
 		}
 		cluster.PullSecret = string(data)
 		cluster.PullSecretPath = ""
@@ -40,7 +39,7 @@ func ParseConfig(data []byte) (*Cluster, error) {
 
 		ami, err := rhcos.AMI(ctx, rhcos.DefaultChannel, cluster.AWS.Region)
 		if err != nil {
-			return nil, fmt.Errorf("failed to determine default AMI: %v", err)
+			return nil, errors.Wrap(err, "failed to determine default AMI")
 		}
 		cluster.EC2AMIOverride = ami
 	}
@@ -52,7 +51,7 @@ func ParseConfig(data []byte) (*Cluster, error) {
 func ParseConfigFile(path string) (*Cluster, error) {
 	data, err := ioutil.ReadFile(path)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to read file")
 	}
 
 	return ParseConfig(data)
@@ -63,7 +62,7 @@ func ParseInternal(data []byte) (*Internal, error) {
 	internal := &Internal{}
 
 	if err := yaml.Unmarshal(data, internal); err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to unmarshal to config.Internal")
 	}
 
 	return internal, nil
@@ -73,7 +72,7 @@ func ParseInternal(data []byte) (*Internal, error) {
 func ParseInternalFile(path string) (*Internal, error) {
 	data, err := ioutil.ReadFile(path)
 	if err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "failed to read file")
 	}
 
 	return ParseInternal(data)