The Proud brothers have each launched separate attempts to change the course of embattled Dye & Durham Ltd. DND-T , a company they built together before a bitter falling out over leadership and strategy. Their latest efforts are echoes of attempts each has pursued before.

Matt Proud, the former chief executive officer of the legal software company that bulked up through acquisitions that swelled its debt levels before he gradually lost the confidence of shareholders, has made what is at least his third bid for D&D this year.

Mr. Proud originally offered to take the company private for $20 a share in February through his private company Plantro Ltd., then for $10.25 this fall. Plantro’s latest bid, sent Wednesday to David Danziger, chairman of the board’s special committee, equals $5.72

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