diff --git a/internal/codespaces/ssh.go b/internal/codespaces/ssh.go
index 4c6ccb6d7..36c8bf5b2 100644
--- a/internal/codespaces/ssh.go
+++ b/internal/codespaces/ssh.go
@@ -70,21 +70,20 @@ func parseSSHArgs(args []string) (cmdArgs, command []string, err error) {
 	for i := 0; i < len(args); i++ {
 		arg := args[i]
 
-		if strings.HasPrefix(arg, "-") {
-			cmdArgs = append(cmdArgs, arg)
-			if len(arg) == 2 && strings.Contains("bcDeFIiLlmOopRSWw", arg[1:2]) {
-				if i++; i == len(args) {
-					return nil, nil, fmt.Errorf("ssh flag: %s requires an argument", arg)
-				}
-
-				cmdArgs = append(cmdArgs, args[i])
-			}
-			continue
+		// if we've started parsing the command, set it to the rest of the args
+		if !strings.HasPrefix(arg, "-") {
+			command = args[i:]
+			break
 		}
 
-		// if we've started parsing the command, set it to the rest of the args
-		command = args[i:]
-		break
+		cmdArgs = append(cmdArgs, arg)
+		if len(arg) == 2 && strings.Contains("bcDeFIiLlmOopRSWw", arg[1:2]) {
+			if i++; i == len(args) {
+				return nil, nil, fmt.Errorf("ssh flag: %s requires an argument", arg)
+			}
+
+			cmdArgs = append(cmdArgs, args[i])
+		}
 	}
 
 	return cmdArgs, command, nil
diff --git a/internal/codespaces/ssh_test.go b/internal/codespaces/ssh_test.go
index c3e1b4c0a..c804f6000 100644
--- a/internal/codespaces/ssh_test.go
+++ b/internal/codespaces/ssh_test.go
@@ -10,7 +10,7 @@ func TestParseSSHArgs(t *testing.T) {
 		Args       []string
 		ParsedArgs []string
 		Command    []string
-		Error      bool
+		Error      string
 	}
 
 	testCases := []testCase{
@@ -69,19 +69,26 @@ func TestParseSSHArgs(t *testing.T) {
 			Args:       []string{"-b"},
 			ParsedArgs: nil,
 			Command:    nil,
-			Error:      true,
+			Error:      "ssh flag: -b requires an argument",
 		},
 	}
 
 	for _, tcase := range testCases {
 		args, command, err := parseSSHArgs(tcase.Args)
-		if !tcase.Error && err != nil {
-			t.Errorf("unexpected error: %v on test case: %#v", err, tcase)
+		if tcase.Error != "" {
+			if err == nil {
+				t.Errorf("expected error and got nil: %#v", tcase)
+			}
+
+			if err.Error() != tcase.Error {
+				t.Errorf("error does not match expected error, got: '%s', expected: '%s'", err.Error(), tcase.Error)
+			}
+
 			continue
 		}
 
-		if tcase.Error && err == nil {
-			t.Errorf("expected error and got nil: %#v", tcase)
+		if err != nil {
+			t.Errorf("unexpected error: %v on test case: %#v", err, tcase)
 			continue
 		}