diff --git a/pkg/cmd/feedback.go b/pkg/cmd/feedback.go
index 8c7e0aab9..546818b6e 100644
--- a/pkg/cmd/feedback.go
+++ b/pkg/cmd/feedback.go
@@ -40,8 +40,7 @@ var feedbackCmd = &cobra.Command{
 			Body  string
 		}{}
 
-		d, err := ghissue.Gather()
-		cobra.CheckErr(err)
+		d := ghissue.Gather()
 
 		diag, err := yaml.Marshal(d)
 		cobra.CheckErr(err)
diff --git a/pkg/cmd/info.go b/pkg/cmd/info.go
index 09949364f..539f7051e 100644
--- a/pkg/cmd/info.go
+++ b/pkg/cmd/info.go
@@ -17,6 +17,9 @@
 package cmd
 
 import (
+	"encoding/json"
+	"fmt"
+
 	"github.com/spf13/cobra"
 
 	"github.com/nitrictech/cli/pkg/ghissue"
@@ -28,8 +31,13 @@ var infoCmd = &cobra.Command{
 	Short: "Gather information about Nitric and the environment",
 	Long:  `Gather information about Nitric and the environment.`,
 	Run: func(cmd *cobra.Command, args []string) {
-		d, err := ghissue.Gather()
-		cobra.CheckErr(err)
-		output.Print(d)
+		d := ghissue.Gather()
+
+		s, err := json.MarshalIndent(d, "", "  ")
+		if err != nil {
+			output.Print(d)
+		} else {
+			fmt.Println(string(s))
+		}
 	},
 }
diff --git a/pkg/cmd/root.go b/pkg/cmd/root.go
index 13b3e2564..2b7b503d5 100644
--- a/pkg/cmd/root.go
+++ b/pkg/cmd/root.go
@@ -28,7 +28,7 @@ import (
 	cmdstack "github.com/nitrictech/cli/pkg/cmd/stack"
 	"github.com/nitrictech/cli/pkg/ghissue"
 	"github.com/nitrictech/cli/pkg/output"
-	"github.com/nitrictech/cli/pkg/preferences"
+	"github.com/nitrictech/cli/pkg/utils"
 )
 
 const usageTemplate = `Nitric - The fastest way to build serverless apps
@@ -62,9 +62,12 @@ var rootCmd = &cobra.Command{
 			pterm.DisableStyling()
 		}
 
-		err := preferences.PromptFeedback()
-		if err != nil {
-			fmt.Println(err.Error())
+		// Ensure the Nitric Home Directory Exists
+		if _, err := os.Stat(utils.NitricHomeDir()); os.IsNotExist(err) {
+			err := os.MkdirAll(utils.NitricHomeDir(), 0o700) // Create the Nitric Home Directory if it's missing
+			if err != nil {
+				cobra.CheckErr(fmt.Errorf("Failed to create nitric home directory. %w", err))
+			}
 		}
 	},
 }
diff --git a/pkg/ghissue/buglink.go b/pkg/ghissue/buglink.go
index 4fc1689de..67c6fa68b 100644
--- a/pkg/ghissue/buglink.go
+++ b/pkg/ghissue/buglink.go
@@ -32,13 +32,14 @@ import (
 )
 
 type Diagnostics struct {
-	OS                      string `json:"os"`
-	Arch                    string `json:"arch"`
-	GoVersion               string `json:"goVersion"`
-	CliVersion              string `json:"cliVersion"`
-	FabricVersion           string `json:"fabricVersion"`
-	ContainerRuntime        string `json:"containerRuntime"`
-	ContainerRuntimeVersion string `json:"containerRuntimeVersion"`
+	OS                      string   `json:"os"`
+	Arch                    string   `json:"arch"`
+	GoVersion               string   `json:"goVersion"`
+	CliVersion              string   `json:"cliVersion"`
+	FabricVersion           string   `json:"fabricVersion"`
+	ContainerRuntime        string   `json:"containerRuntime"`
+	ContainerRuntimeVersion string   `json:"containerRuntimeVersion"`
+	DetectedErrors          []string `json:"detectedErrors"`
 }
 
 type GHIssue struct {
@@ -49,27 +50,29 @@ type GHIssue struct {
 }
 
 var diag = Diagnostics{
-	OS:            runtime.GOOS,
-	Arch:          runtime.GOARCH,
-	GoVersion:     runtime.Version(),
-	CliVersion:    utils.Version,
-	FabricVersion: project.DefaultMembraneVersion,
+	OS:             runtime.GOOS,
+	Arch:           runtime.GOARCH,
+	GoVersion:      runtime.Version(),
+	CliVersion:     utils.Version,
+	FabricVersion:  project.DefaultMembraneVersion,
+	DetectedErrors: make([]string, 0),
 }
 
-func Gather() (*Diagnostics, error) {
+func Gather() *Diagnostics {
 	ce, err := containerengine.Discover()
 	if err != nil {
-		return &diag, err
+		diag.DetectedErrors = append(diag.DetectedErrors, err.Error())
+		return &diag
 	}
 
 	diag.ContainerRuntime = ce.Type()
 	diag.ContainerRuntimeVersion = ce.Version()
 
-	return &diag, nil
+	return &diag
 }
 
 func BugLink(err interface{}) string {
-	d, _ := Gather()
+	d := Gather()
 	issue := GHIssue{
 		Diagnostics: *d,
 		Error:       fmt.Sprint(err),
diff --git a/pkg/preferences/userpreferences.go b/pkg/preferences/userpreferences.go
index 15093b115..767697dab 100644
--- a/pkg/preferences/userpreferences.go
+++ b/pkg/preferences/userpreferences.go
@@ -89,7 +89,7 @@ func ReadUserPreferences() (*UserPreferences, error) {
 func (up *UserPreferences) WriteToFile() error {
 	file, err := os.Create(utils.NitricPreferencesPath())
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to update user preferences.\n\tUnable to access file: %s", utils.NitricPreferencesPath())
 	}
 	defer file.Close()