diff --git a/command/apply.go b/command/apply.go
index 94f7d129c6..9b9b898716 100644
--- a/command/apply.go
+++ b/command/apply.go
@@ -8,6 +8,7 @@ import (
 	"sort"
 	"strings"
 
+	"github.com/hashicorp/errwrap"
 	"github.com/hashicorp/go-getter"
 	"github.com/hashicorp/terraform/backend"
 	"github.com/hashicorp/terraform/config"
@@ -130,7 +131,8 @@ func (c *ApplyCommand) Run(args []string) int {
 	if plan == nil {
 		mod, err = c.Module(configPath)
 		if err != nil {
-			c.Ui.Error(fmt.Sprintf("Failed to load root config module: %s", err))
+			err = errwrap.Wrapf("Failed to load root config module: {{err}}", err)
+			c.showDiagnostics(err)
 			return 1
 		}
 	}
diff --git a/command/init.go b/command/init.go
index b81109ec2c..28e4ffbbb7 100644
--- a/command/init.go
+++ b/command/init.go
@@ -155,8 +155,10 @@ func (c *InitCommand) Run(args []string) int {
 	if flagGet || flagBackend {
 		conf, err := c.Config(path)
 		if err != nil {
-			c.Ui.Error(fmt.Sprintf(
-				"Error loading configuration: %s", err))
+			// Since this may be the user's first ever interaction with Terraform,
+			// we'll provide some additional context in this case.
+			c.Ui.Error(strings.TrimSpace(errInitConfigError))
+			c.showDiagnostics(err)
 			return 1
 		}
 
@@ -551,6 +553,13 @@ func (c *InitCommand) Synopsis() string {
 	return "Initialize a Terraform working directory"
 }
 
+const errInitConfigError = `
+There are some problems with the configuration, described below.
+
+The Terraform configuration must be valid before initialization so that
+Terraform can determine which modules and providers need to be installed.
+`
+
 const errInitCopyNotEmpty = `
 The working directory already contains files. The -from-module option requires
 an empty directory into which a copy of the referenced module will be placed.
diff --git a/command/plan.go b/command/plan.go
index f353651977..036e6fe35b 100644
--- a/command/plan.go
+++ b/command/plan.go
@@ -5,6 +5,7 @@ import (
 	"fmt"
 	"strings"
 
+	"github.com/hashicorp/errwrap"
 	"github.com/hashicorp/terraform/backend"
 	"github.com/hashicorp/terraform/config"
 	"github.com/hashicorp/terraform/config/module"
@@ -73,7 +74,8 @@ func (c *PlanCommand) Run(args []string) int {
 	if plan == nil {
 		mod, err = c.Module(configPath)
 		if err != nil {
-			c.Ui.Error(fmt.Sprintf("Failed to load root config module: %s", err))
+			err = errwrap.Wrapf("Failed to load root config module: {{err}}", err)
+			c.showDiagnostics(err)
 			return 1
 		}
 	}
diff --git a/command/refresh.go b/command/refresh.go
index 1949b54fe4..b6ae6b8543 100644
--- a/command/refresh.go
+++ b/command/refresh.go
@@ -5,6 +5,7 @@ import (
 	"fmt"
 	"strings"
 
+	"github.com/hashicorp/errwrap"
 	"github.com/hashicorp/terraform/backend"
 	"github.com/hashicorp/terraform/config"
 	"github.com/hashicorp/terraform/terraform"
@@ -43,7 +44,8 @@ func (c *RefreshCommand) Run(args []string) int {
 	// Load the module
 	mod, err := c.Module(configPath)
 	if err != nil {
-		c.Ui.Error(fmt.Sprintf("Failed to load root config module: %s", err))
+		err = errwrap.Wrapf("Failed to load root config module: {{err}}", err)
+		c.showDiagnostics(err)
 		return 1
 	}
 
diff --git a/command/validate.go b/command/validate.go
index d5ec580fe0..bd0af057bc 100644
--- a/command/validate.go
+++ b/command/validate.go
@@ -91,21 +91,19 @@ Options:
 func (c *ValidateCommand) validate(dir string, checkVars bool) int {
 	cfg, err := config.LoadDir(dir)
 	if err != nil {
-		c.Ui.Error(fmt.Sprintf(
-			"Error loading files %v\n", err.Error()))
+		c.showDiagnostics(err)
 		return 1
 	}
 	err = cfg.Validate()
 	if err != nil {
-		c.Ui.Error(fmt.Sprintf(
-			"Error validating: %v\n", err.Error()))
+		c.showDiagnostics(err)
 		return 1
 	}
 
 	if checkVars {
 		mod, err := c.Module(dir)
 		if err != nil {
-			c.Ui.Error(fmt.Sprintf("Failed to load root config module: %s", err))
+			c.showDiagnostics(err)
 			return 1
 		}
 
@@ -114,7 +112,7 @@ func (c *ValidateCommand) validate(dir string, checkVars bool) int {
 
 		tfCtx, err := terraform.NewContext(opts)
 		if err != nil {
-			c.Ui.Error(fmt.Sprintf("Error: %v\n", err.Error()))
+			c.showDiagnostics(err)
 			return 1
 		}