Whether an agreement is a mortgage by conditional sale or sale with an option to repurchase is a vexed question to be considered in the facts of each case. The essentials of an agreement, to qualify as a mortgage by conditional sale, can succinctly be summarized. An ostensible sale with transfer of possession and ownership, but containing a clause for reconveyance in accordance with Section 58(c) of the Act, will clothe the agreement as a mortgage by conditional sale. Referring to Section 58(c) of the Transfer of Property Act the observed, “A deeming fiction was added in the negative that a transaction shall not be deemed to be a mortgage unless the condition for reconveyance is contained in the document which purports to effect the sale.” The issue under adjudication was whether the transaction between the parties was an absolute sale of the property or it was a mortgage. The court relied upon the case Bishwanath Prasad Singh v. Rajendra Prasad and Anr, 2006 SC and held that A bare perusal of the said provision clearly shows that a mortgage by conditional sale must be evidenced by one document whereas a sale with condition of retransfer may be evidenced by more than one document. A sale with a condition of retransfer is not a mortgage. It is not a partial transfer. By reason of such a transfer all rights have been transferred reserving only a personal right to the purchaser and such a personal right would be lost unless the same is exercised within the stipulated time. The execution of separate agreement for reconveyance, either contemporaneously or subsequently, shall militate against the agreement being mortgaged by conditional sale. There must exist a debtor and creditor relationship. The valuation of the property, and the transaction value, along with the duration of time for reconveyance, are important considerations to decide the nature of the agreement. There will have to be a cumulative consideration of these factors, along with the recitals in the agreement, intention of the parties, coupled with other attendant circumstances, considered in a holistic manner. The language used in the agreement may not always be conclusive. (Extract from Prakash (Dead) By LR. V. G. Aradhya & Ors, 2023 SC)