diff --git a/pkg/bootstrap/docker/dockerhelper/helper.go b/pkg/bootstrap/docker/dockerhelper/helper.go
index 0718232be54e..0acbfcdf3034 100644
--- a/pkg/bootstrap/docker/dockerhelper/helper.go
+++ b/pkg/bootstrap/docker/dockerhelper/helper.go
@@ -1,12 +1,14 @@
 package dockerhelper
 
 import (
+	"bytes"
 	"encoding/json"
 	"errors"
 	"fmt"
 	"io"
 	"net"
 	"net/url"
+	"strconv"
 	"strings"
 
 	"github.com/blang/semver"
@@ -207,6 +209,22 @@ func (h *Helper) HostIP() string {
 	return ""
 }
 
+func (h *Helper) ContainerLog(container string, numLines int) string {
+	output := &bytes.Buffer{}
+	err := h.client.Logs(docker.LogsOptions{
+		Container:    container,
+		Tail:         strconv.Itoa(numLines),
+		OutputStream: output,
+		ErrorStream:  output,
+		Stdout:       true,
+		Stderr:       true,
+	})
+	if err != nil {
+		glog.V(1).Infof("Error getting container %q log: %v", container, err)
+	}
+	return output.String()
+}
+
 func (h *Helper) StopAndRemoveContainer(container string) error {
 	err := h.client.StopContainer(container, 10)
 	if err != nil {
diff --git a/pkg/bootstrap/docker/errors/errors.go b/pkg/bootstrap/docker/errors/errors.go
index f1ceb8f79fd0..71f23a02751a 100644
--- a/pkg/bootstrap/docker/errors/errors.go
+++ b/pkg/bootstrap/docker/errors/errors.go
@@ -15,6 +15,7 @@ type Error interface {
 	error
 	WithCause(error) Error
 	WithSolution(string, ...interface{}) Error
+	WithDetails(string) Error
 }
 
 func NewError(msg string, args ...interface{}) Error {
@@ -42,6 +43,10 @@ func (e *internalError) Solution() string {
 	return e.solution
 }
 
+func (e *internalError) Details() string {
+	return e.details
+}
+
 func (e *internalError) WithCause(err error) Error {
 	e.cause = err
 	return e
diff --git a/pkg/bootstrap/docker/openshift/admin.go b/pkg/bootstrap/docker/openshift/admin.go
index 6d047bc745e9..4dfb253656fd 100644
--- a/pkg/bootstrap/docker/openshift/admin.go
+++ b/pkg/bootstrap/docker/openshift/admin.go
@@ -35,7 +35,7 @@ func (h *Helper) InstallRegistry(kubeClient kclient.Interface, f *clientcmd.Fact
 		return nil
 	}
 	if !apierrors.IsNotFound(err) {
-		return errors.NewError("error retrieving docker registry service").WithCause(err)
+		return errors.NewError("error retrieving docker registry service").WithCause(err).WithDetails(h.OriginLog())
 	}
 	imageTemplate := variable.NewDefaultImageTemplate()
 	imageTemplate.Format = images
@@ -53,7 +53,10 @@ func (h *Helper) InstallRegistry(kubeClient kclient.Interface, f *clientcmd.Fact
 	output := &bytes.Buffer{}
 	err = registry.RunCmdRegistry(f, cmd, output, cfg, []string{})
 	glog.V(4).Infof("Registry command output:\n%s", output.String())
-	return err
+	if err != nil {
+		return errors.NewError("cannot install registry").WithCause(err).WithDetails(h.OriginLog())
+	}
+	return nil
 }
 
 // InstallRouter installs a default router on the OpenShift server
@@ -63,6 +66,9 @@ func (h *Helper) InstallRouter(kubeClient kclient.Interface, f *clientcmd.Factor
 		// Router service already exists, nothing to do
 		return nil
 	}
+	if !apierrors.IsNotFound(err) {
+		return errors.NewError("error retrieving router service").WithCause(err).WithDetails(h.OriginLog())
+	}
 
 	masterDir := filepath.Join(configDir, "master")
 
@@ -71,18 +77,18 @@ func (h *Helper) InstallRouter(kubeClient kclient.Interface, f *clientcmd.Factor
 	routerSA.Name = "router"
 	_, err = kubeClient.ServiceAccounts("default").Create(routerSA)
 	if err != nil {
-		return errors.NewError("cannot create router service account").WithCause(err)
+		return errors.NewError("cannot create router service account").WithCause(err).WithDetails(h.OriginLog())
 	}
 
 	// Add router SA to privileged SCC
 	privilegedSCC, err := kubeClient.SecurityContextConstraints().Get("privileged")
 	if err != nil {
-		return errors.NewError("cannot retrieve privileged SCC").WithCause(err)
+		return errors.NewError("cannot retrieve privileged SCC").WithCause(err).WithDetails(h.OriginLog())
 	}
 	privilegedSCC.Users = append(privilegedSCC.Users, serviceaccount.MakeUsername("default", "router"))
 	_, err = kubeClient.SecurityContextConstraints().Update(privilegedSCC)
 	if err != nil {
-		return errors.NewError("cannot update privileged SCC").WithCause(err)
+		return errors.NewError("cannot update privileged SCC").WithCause(err).WithDetails(h.OriginLog())
 	}
 
 	// Create router cert
@@ -134,7 +140,10 @@ func (h *Helper) InstallRouter(kubeClient kclient.Interface, f *clientcmd.Factor
 	cmd.SetOutput(output)
 	err = router.RunCmdRouter(f, cmd, output, cfg, []string{})
 	glog.V(4).Infof("Router command output:\n%s", output.String())
-	return err
+	if err != nil {
+		return errors.NewError("cannot install router").WithCause(err).WithDetails(h.OriginLog())
+	}
+	return nil
 }
 
 // catFiles concatenates multiple source files into a single destination file
diff --git a/pkg/bootstrap/docker/openshift/errors.go b/pkg/bootstrap/docker/openshift/errors.go
index 4dbca725e3e1..35ab5fc769d6 100644
--- a/pkg/bootstrap/docker/openshift/errors.go
+++ b/pkg/bootstrap/docker/openshift/errors.go
@@ -2,17 +2,19 @@ package openshift
 
 import (
 	"fmt"
+
+	"github.com/openshift/origin/pkg/bootstrap/docker/errors"
 )
 
 // ErrOpenShiftFailedToStart is thrown when the OpenShift server failed to start
-func ErrOpenShiftFailedToStart(container string) error {
-	return fmt.Errorf("Could not start OpenShift container %q", container)
+func ErrOpenShiftFailedToStart(container string) errors.Error {
+	return errors.NewError("could not start OpenShift container %q", container)
 }
 
 // ErrTimedOutWaitingForStart is thrown when the OpenShift server can't be pinged after reasonable
 // amount of time.
-func ErrTimedOutWaitingForStart(container string) error {
-	return fmt.Errorf("Could not start OpenShift container %q", container)
+func ErrTimedOutWaitingForStart(container string) errors.Error {
+	return errors.NewError("timed out waiting for OpenShift container %q", container)
 }
 
 type errPortsNotAvailable struct {
diff --git a/pkg/bootstrap/docker/openshift/helper.go b/pkg/bootstrap/docker/openshift/helper.go
index 1242673faa43..d2e48ed984a2 100644
--- a/pkg/bootstrap/docker/openshift/helper.go
+++ b/pkg/bootstrap/docker/openshift/helper.go
@@ -268,14 +268,14 @@ func (h *Helper) Start(opt *StartOptions, out io.Writer) (string, error) {
 		return "", errors.NewError("cannot get state of OpenShift container %s", h.containerName).WithCause(err)
 	}
 	if !running {
-		return "", ErrOpenShiftFailedToStart(h.containerName)
+		return "", ErrOpenShiftFailedToStart(h.containerName).WithDetails(h.OriginLog())
 	}
 
 	// Wait until the API server is listening
 	fmt.Fprintf(out, "Waiting for API server to start listening\n")
 	masterHost := fmt.Sprintf("%s:8443", opt.ServerIP)
 	if err = cmdutil.WaitForSuccessfulDial(true, "tcp", masterHost, 200*time.Millisecond, 1*time.Second, serverUpTimeout); err != nil {
-		return "", ErrTimedOutWaitingForStart(h.containerName)
+		return "", ErrTimedOutWaitingForStart(h.containerName).WithDetails(h.OriginLog())
 	}
 	// Check for healthz endpoint to be ready
 	client, err := masterHTTPClient(configDir)
@@ -285,7 +285,7 @@ func (h *Helper) Start(opt *StartOptions, out io.Writer) (string, error) {
 	for {
 		resp, ierr := client.Get(h.healthzReadyURL(opt.ServerIP))
 		if ierr != nil {
-			return "", errors.NewError("cannot access master readiness URL %s", h.healthzReadyURL(opt.ServerIP)).WithCause(err)
+			return "", errors.NewError("cannot access master readiness URL %s", h.healthzReadyURL(opt.ServerIP)).WithCause(err).WithDetails(h.OriginLog())
 		}
 		if resp.StatusCode == http.StatusOK {
 			break
@@ -300,12 +300,20 @@ func (h *Helper) Start(opt *StartOptions, out io.Writer) (string, error) {
 		if rerr == nil {
 			responseBody = string(body)
 		}
-		return "", errors.NewError("server is not ready. Response (%d): %s", resp.StatusCode, responseBody).WithCause(ierr)
+		return "", errors.NewError("server is not ready. Response (%d): %s", resp.StatusCode, responseBody).WithCause(ierr).WithDetails(h.OriginLog())
 	}
 	fmt.Fprintf(out, "OpenShift server started\n")
 	return configDir, nil
 }
 
+func (h *Helper) OriginLog() string {
+	log := h.dockerHelper.ContainerLog(h.containerName, 10)
+	if len(log) > 0 {
+		return fmt.Sprintf("Last 10 lines of %q container log:\n%s\n", h.containerName, log)
+	}
+	return fmt.Sprintf("No log available from %q container\n", h.containerName)
+}
+
 func (h *Helper) healthzReadyURL(ip string) string {
 	return fmt.Sprintf("%s/healthz/ready", h.Master(ip))
 }
diff --git a/pkg/bootstrap/docker/up.go b/pkg/bootstrap/docker/up.go
index 68d812600698..8031ef25a470 100644
--- a/pkg/bootstrap/docker/up.go
+++ b/pkg/bootstrap/docker/up.go
@@ -611,7 +611,7 @@ func (c *ClientStartConfig) importObjects(out io.Writer, locations map[string]st
 		glog.V(2).Infof("Importing %s from %s", name, location)
 		err = openshift.ImportObjects(f, openShiftNamespace, location)
 		if err != nil {
-			return err
+			return errors.NewError("cannot import %s", name).WithCause(err).WithDetails(c.OpenShiftHelper().OriginLog())
 		}
 	}
 	return nil