The town council says upcoming system changes means that its current Pay & Display ticket machines on Central Car Park will become obsolete.
That, combined with issues over the amount of cash that can be banked from the machines, have led the council to look for a new system.
The council is also looking at upgrading the toilets at the car park.
But there are no plans to look at changing the entrance and exit, something residents have been calling for for many years.
A report to this Wednesday's council meeting said officers have been looking at ways that the amount of cash used for payments can be reduced.
Also, the council was informed that mobile network operators were planning to decommission their 2G and 3G networks to push resources to 4G and 5G technology.
Henry Teuma, operations manager, said: "Vodafone, the service provider to the SIM cards in our ticket machine modems, will be starting to decommission its 3G network from February 2023.
"All the Pay & Display ticket machines currently host a 3G modem and therefore all 15 will need to be changed. The timeframe as to when the 3G network in Oswestry will be decommissioned is unknown and is reliant on an announcement by Vodafone, however it has stated that the entire 3G network will be decommissioned by December 2023.
"As all machines will require an upgrade to host a 4G modem, there is also an opportunity to introduce card machine payments within some of the ticket machines."
At the moment the public can pay for parking in two ways, by cash or via an app.
"Adding in the option to pay by card will give members of the public a third option to pay for a ticket and modernise the process. All of the machines will have the option to pay by cash or by card."
To upgrade all 15 machines and have three with card payment would cost £9,669. To upgrade all of them with card payments would cost just over £21,000.
There would also be an 18p transaction fee for each ticket purchased.
Councillors are being recommended to go for the three card payment machine option using reserves.
The council is also looking at completely upgrading the Central car park toilets.
A report says the organisation Healthmatic has recommended a cubicle system not defined by gender.
It says that four cubicles would provide adequate provision for 60,000 uses. Income figures highlight that current usage is in the region of 50,000.
Councillors will discuss proving a Changing Space facility for people with extra needs as part of the upgrade.