Right-back Sears has looked the part for the Bucks but his one-month stay finishes after the home game against Ashton United on Saturday.
It is understood Cowan would like the 19-year-old to remain at the New Bucks Head for at least another month, but it has to suit everyone at Telford – and parent club Salop.
"I'm really not sure. I haven't spoken to John (Askey) or anyone at Shrewsbury," said Cowan, when asked if the Bucks were any closer to extending Sears' stay.
"I'll be sitting down with the chairman.
"His final game is against Ashton so I'll know more after this week."
It is believed Town would prefer Sears to carry on with the Bucks and be playing regularly as opposed to being a bit-part player under Askey.
Salop are believed to be monitoring his progress closely though as, at the moment, James Bolton is their only natural right-back.
Sears spent last season at Welsh Premier side Newtown and ended up winning their players’ player of the year award. He is contracted at Montgomery Waters Meadow until next summer.
Meanwhile, progress on a loan move away from Telford for fellow defender Zak Lilly has slowed.
Cowan initially wanted to get the 20-year-old, who has gone from a forward to a centre-half over the summer, out to get some game time by the end of last week.
He was at the home win against Chester on Saturday and the draw at Leamington on Monday though, despite not being named in either squad.
A loan away for Lilly could depend on whether Sears ends up with the Bucks for longer or not.
If Sears does not stay after the initial month, Cowan may be reluctant to let Lilly leave temporarily as, with Steph Morley dealing with a calf problem, it would potentially leave Telford light at the back.
Lilly has previously had loan spells at Rushall Olympic, Leamington, Romulus and Sutton Coldfield.
The former Thomas Telford student and England schoolboys star is tied down to the Bucks until the end of the season.