diff --git a/internals/repl/repl.go b/internals/repl/repl.go
index 4e2de24..79e6483 100644
--- a/internals/repl/repl.go
+++ b/internals/repl/repl.go
@@ -37,6 +37,10 @@ func Run() {
 			fmt.Println("Syntax error, could not parse statement")
 		case PrepareUnrecognised:
 			fmt.Printf("Unrecognised keyword at the start of '%s'.\n", inputBuffer.Buffer)
+		case PrepareTooManyArgs:
+			fmt.Printf("Too many arguments in the insert statement '%v'\n", inputBuffer.Buffer)
+		case PrepareValueTooLong:
+			fmt.Printf("Values for either username or email are too long\n")
 		}
 
 		switch statement.ExecuteStatement(table) {
diff --git a/internals/vm/vm.go b/internals/vm/vm.go
index a9b93ab..dec21f6 100644
--- a/internals/vm/vm.go
+++ b/internals/vm/vm.go
@@ -4,6 +4,8 @@ import (
 	"encoding/binary"
 	"fmt"
 	"os"
+	"slices"
+	"strconv"
 	"strings"
 
 	. "godb/internals/buffer"
@@ -21,6 +23,8 @@ type PrepareResults int
 const (
 	PrepareSuccess PrepareResults = iota
 	PrepareUnrecognised
+	PrepareTooManyArgs
+	PrepareValueTooLong
 	PrepareSyntaxError
 )
 
@@ -151,19 +155,45 @@ func DoMetaCommands(inputBuffer *InputBuffer) MetaCommandResults {
 	return metacommand
 }
 
+func (statement *Statement) perpareInsert(inputBuffer *InputBuffer) PrepareResults {
+	inputs := strings.Split(inputBuffer.Buffer, " ")[1:]
+	if len(inputs) < 3 {
+		return PrepareSyntaxError
+	}
+	if len(inputs) > 3 {
+		return PrepareTooManyArgs
+	}
+	if slices.Contains(inputs, "null") || slices.Contains(inputs, "NULL") || slices.Contains(inputs, "Null") || slices.Contains(inputs, " ") {
+		return PrepareSyntaxError
+	}
+
+	tid, err := strconv.ParseUint(inputs[0], 10, 0)
+	if err != nil {
+		// fmt.Printf("supplied ID: %v isn't acceptable, please correct and retry\n", inputs[0])
+		return PrepareSyntaxError
+	}
+	id := uint(tid)
+	if len(inputs[1]) > usernameSize {
+		// fmt.Printf("%v is too long for username\n", inputs[1])
+		return PrepareValueTooLong
+	}
+	if len(inputs[2]) > emailSize {
+		// fmt.Printf("%v is too long for email\n", inputs[2])
+		return PrepareValueTooLong
+	}
+
+	statement.row.id = id
+	statement.row.username = inputs[1]
+	statement.row.email = inputs[2]
+
+	statement.stype = StatementInsert
+	return PrepareSuccess
+}
+
 func (statement *Statement) PrepareStatements(inputBuffer *InputBuffer) PrepareResults {
 	statement.stype = StatementUnrecognized
 	if strings.HasPrefix(inputBuffer.Buffer, "insert") {
-		argsAssigned, err := fmt.Sscanf(inputBuffer.Buffer, "insert %d %s %s", &statement.row.id, &statement.row.username, &statement.row.email)
-		if err != nil {
-			fmt.Println("error parsing insert statement")
-			fmt.Println(err.Error())
-		}
-		if err != nil || argsAssigned > 3 {
-			return PrepareSyntaxError
-		}
-		statement.stype = StatementInsert
-		return PrepareSuccess
+		return statement.perpareInsert(inputBuffer)
 	}
 	if inputBuffer.Buffer == "select" {
 		statement.stype = StatementSelect
diff --git a/tests/main_test.go b/tests/main_test.go
index 029e0b7..94a3b6d 100644
--- a/tests/main_test.go
+++ b/tests/main_test.go
@@ -106,3 +106,31 @@ func TestTableFull(t *testing.T) {
 		t.Errorf("Our Tables max capacity is 1300 rows, but we're able to insert %v\n", len(results))
 	}
 }
+
+func TestMaxLengthForValues(t *testing.T) {
+	commands := []string{"insert 0 " + strings.Repeat("n", 32) + " " + strings.Repeat("n", 255), ".exit"}
+	expected := []string{"godb > Executed.", "godb > bye!"}
+
+	results := runner(commands, t)
+	for i := range results {
+		results[i] = strings.ReplaceAll(results[i], "\n", "")
+	}
+
+	if !slices.Equal(expected, results) {
+		t.Errorf("Output Mismatch\nExpected: %v\nGot: %v\n", expected, results)
+	}
+}
+
+func TestOverMaxLengthValues(t *testing.T) {
+	commands := []string{"insert 0 " + strings.Repeat("n", 42) + " " + strings.Repeat("n", 275), ".exit"}
+	expected := []string{"godb > Values for either username or email are too long", "godb > bye!"}
+
+	results := runner(commands, t)
+	for i := range results {
+		results[i] = strings.ReplaceAll(results[i], "\n", "")
+	}
+
+	if !slices.Equal(expected, results) {
+		t.Errorf("Output Mismatch\nExpected: %v\nGot: %v\n", expected, results)
+	}
+}