Transit Stamp Ext. Question

[Moonrakers]

I have a transit stamp (14 days) that is due to expire next week which I am planning to extend for 60 days at immigration based on my marriage to a Thai, my previous visa was a Non-O extended to one year based on marriage.

Getting the extension done before the expiry is going to be difficult. So my question is: If I was to go to immigration a couple of days over, will I be able to pay the fine AND get the extension or do I waive the right to the extension by going on overstay?

Thanks.

[Moonrakers]

Or plan B:

If I miss the extension (expiry) deadline and cross the border again, returning with another 14 day transit stamp am I able to get a 60 day extension from that?

[Mario2008]

Keep it legal and safe. Overstay means your permission to stay has expired. They might or not might fine you and give you the extension, that is up to the immigration officer. Best is to get the 60 day extention now, you will not lose any days by that as it will start from the day your current extension ends. Otherwise leave the country and get a new visa exempt entry and extend that one.