diff --git a/cmd/sqlcmd/sqlcmd.go b/cmd/sqlcmd/sqlcmd.go
index 7d69b24b..227cdbd6 100644
--- a/cmd/sqlcmd/sqlcmd.go
+++ b/cmd/sqlcmd/sqlcmd.go
@@ -294,6 +294,9 @@ func Execute(version string) {
 // We need to rewrite the arguments to add -i and -v in front of each space-delimited value to be Cobra-friendly.
 // For flags like -r we need to inject the default value if the user omits it
 func convertOsArgs(args []string) (cargs []string) {
+	// Pre-process to handle special help flag cases
+	args = preprocessHelpFlags(args)
+
 	flag := ""
 	first := true
 	for i, a := range args {
@@ -323,6 +326,63 @@ func convertOsArgs(args []string) (cargs []string) {
 	return
 }
 
+// preprocessHelpFlags handles special cases for help flags to improve user experience:
+// 1. Converts "-help" to "--help" since "-help" would be parsed as "-h elp"
+// 2. Converts "-h" without an argument to "-?" to show help, since many users expect
+//    "-h" to show help (common in other CLI tools), even though in sqlcmd "-h" is
+//    traditionally used to set header count. When "-h" has a following number, it's
+//    left as-is to maintain compatibility with the traditional behavior.
+func preprocessHelpFlags(args []string) []string {
+	result := make([]string, 0, len(args))
+	for i := 0; i < len(args); i++ {
+		arg := args[i]
+
+		// Convert "-help" to "--help"
+		if arg == "-help" {
+			result = append(result, "--help")
+			continue
+		}
+
+		// Handle "-h" without an argument: convert to "-?" to show help
+		if arg == "-h" {
+			// Check if next arg exists
+			hasNextArg := i+1 < len(args)
+			nextIsNumber := false
+			nextIsFlag := false
+			if hasNextArg {
+				nextArg := args[i+1]
+				// Check if next arg looks like a number (including negative numbers)
+				// This must be checked before checking if it's a flag, because
+				// negative numbers start with '-'
+				_, err := strconv.Atoi(nextArg)
+				nextIsNumber = err == nil
+				
+				// Check if next arg is a flag (starts with '-' but is not a number)
+				if !nextIsNumber && len(nextArg) > 0 && nextArg[0] == '-' {
+					nextIsFlag = true
+				}
+			}
+			
+			// If -h is followed by a number, keep it as-is (header count)
+			// Otherwise, convert to -? (show help) and consume any non-numeric, non-flag argument
+			if !nextIsNumber {
+				result = append(result, "-?")
+				// If there was a following non-numeric, non-flag argument, consume it
+				// (Don't consume flags, as they should be processed normally)
+				if hasNextArg && !nextIsFlag {
+					i++
+				}
+			} else {
+				result = append(result, arg)
+			}
+			continue
+		}
+		
+		result = append(result, arg)
+	}
+	return result
+}
+
 // If args[i] is the given flag and args[i+1] is another flag, returns the value to append after the flag
 func checkDefaultValue(args []string, i int) (val string) {
 	flags := map[rune]string{
diff --git a/cmd/sqlcmd/sqlcmd_test.go b/cmd/sqlcmd/sqlcmd_test.go
index 511816b2..d04d625b 100644
--- a/cmd/sqlcmd/sqlcmd_test.go
+++ b/cmd/sqlcmd/sqlcmd_test.go
@@ -72,6 +72,15 @@ func TestValidCommandLineToArgsConversion(t *testing.T) {
 		{[]string{"-h", "2", "-?"}, func(args SQLCmdArguments) bool {
 			return args.Help && args.Headers == 2
 		}},
+		{[]string{"-h"}, func(args SQLCmdArguments) bool {
+			return args.Help
+		}},
+		{[]string{"-help"}, func(args SQLCmdArguments) bool {
+			return args.Help
+		}},
+		{[]string{"-h", "abc"}, func(args SQLCmdArguments) bool {
+			return args.Help
+		}},
 		{[]string{"-u", "-A"}, func(args SQLCmdArguments) bool {
 			return args.UnicodeOutputFile && args.DedicatedAdminConnection
 		}},
@@ -584,6 +593,36 @@ func TestConvertOsArgs(t *testing.T) {
 			[]string{"-X", "-k2"},
 			[]string{"-X", "0", "-k2"},
 		},
+		{
+			"-h without argument converts to -? for help",
+			[]string{"-h"},
+			[]string{"-?"},
+		},
+		{
+			"-h with number keeps -h for headers",
+			[]string{"-h", "5"},
+			[]string{"-h", "5"},
+		},
+		{
+			"-h with negative number keeps -h for headers",
+			[]string{"-h", "-1"},
+			[]string{"-h", "-1"},
+		},
+		{
+			"-help converts to --help",
+			[]string{"-help"},
+			[]string{"--help"},
+		},
+		{
+			"-h followed by flag converts to -? for help",
+			[]string{"-h", "-E"},
+			[]string{"-?", "-E"},
+		},
+		{
+			"-h followed by non-numeric converts to -? for help (consuming the non-numeric arg)",
+			[]string{"-h", "abc"},
+			[]string{"-?"},
+		},
 	}
 	for _, c := range tests {
 		t.Run(c.name, func(t *testing.T) {