diff --git a/pkg/helpers/helpers_strings_test.go b/pkg/helpers/helpers_strings_test.go
new file mode 100644
index 00000000000..4bdf31dc9cc
--- /dev/null
+++ b/pkg/helpers/helpers_strings_test.go
@@ -0,0 +1,19 @@
+// Copyright (c) Microsoft Corporation.
+// Licensed under the MIT License.
+
+package helpers
+
+import (
+	"testing"
+	"unicode"
+)
+
+// TestGenerateRandomUsername tests whether the username generated will ever start with a non letter
+func TestGenerateRandomUsername(t *testing.T) {
+	for i := 0; i < 1000; i++ {
+		u := GenerateRandomUsername(10)
+		if !unicode.IsLetter(rune(u[0])) {
+			t.Errorf("index 0 of username '%s' is not a letter '%s'", u, string(u[0]))
+		}
+	}
+}
diff --git a/pkg/helpers/labels.go b/pkg/helpers/labels.go
index 7647a895242..690bf029448 100644
--- a/pkg/helpers/labels.go
+++ b/pkg/helpers/labels.go
@@ -15,7 +15,7 @@ func LabelsToTags(in map[string]string) map[string]*string {
 		newK := k
 		value := v
 		if strings.ContainsAny(k, "<>%/?\\") {
-			newK = ReplaceAny(k, []string{"<", ">", "%", "/", "\\\\", "?"})
+			newK = ReplaceAny(k, []string{"<", ">", "%", "/", "\\\\", "\\?"})
 		}
 		out[newK] = &value
 	}
diff --git a/pkg/helpers/stringhelper.go b/pkg/helpers/stringhelper.go
index f291e29689d..7f150a24993 100644
--- a/pkg/helpers/stringhelper.go
+++ b/pkg/helpers/stringhelper.go
@@ -18,13 +18,15 @@ import (
 )
 
 const (
-	passwordLength  = 16
-	passwordChars   = lowerAlphaChars + upperAlphaChars + numberChars + specialChars
-	usernameChars   = lowerAlphaChars + upperAlphaChars + numberChars
+	passwordLength = 16
+
 	lowerAlphaChars = "abcdefghijklmnopqrstuvwxyz"
 	upperAlphaChars = "ABCDEFGHIJKLMNOPQRSTUVWXYZ"
 	numberChars     = "0123456789"
 	specialChars    = "!@#$%^&*"
+	passwordChars   = lowerAlphaChars + upperAlphaChars + numberChars + specialChars
+	usernameChars   = lowerAlphaChars + upperAlphaChars + numberChars
+	allCaseAlpha    = lowerAlphaChars + upperAlphaChars
 )
 
 var seededRand = NewSeeded()
@@ -96,19 +98,13 @@ func GenerateRandomUsername(n int) string {
 	b := make([]byte, n)
 
 	// ensure first char is alpha
-	b[0] = lowerAlphaChars[seededRand.Intn(len(lowerAlphaChars))]
+	b[0] = allCaseAlpha[seededRand.Intn(len(allCaseAlpha))]
 
 	for i := 1; i < n; i++ {
 		b[i] = usernameChars[seededRand.Intn(len(usernameChars))]
 	}
-	// For good measure, shuffle the elements of the entire []byte so that
-	// the 0 character isn't predicatably lowercase, etc...
-	for i := range b {
-		j := seededRand.Intn(len(b))
-		b[i], b[j] = b[j], b[i]
-	}
-	return string(b)
 
+	return string(b)
 }
 
 // GenerateRandomPassword - helper function to generate random password for sql server