The article examines the legal and technical aspects of determining the time of signing for both hand-written and electronic signatures. Of particular relevance in light of the widespread utilisation of electronic signatures in Estonia, involving both government-issued and private-sector e-signatures, it explores how signatures are linked to the time of transactions and whether the time of signing affects the validity of signatures under Estonian and European Union law. The paper discusses the general principle of freedom of form in transactions, highlighting the formal requirements imposed by law for certain transactions and wills, with special focus on comparing the traditional analogue world with the digital environment. Additionally, a review of recent amendments to the eIDAS Regulation examines their impact on the union’s electronic-signature ecosystem. Discussion addresses technical challenges also, with specific regard to linking a signature to the time of the transaction and the legal implications of timestamping in the domain of electronic signatures. For broader context, the insight is informed by comparison with Norway, another member of the European Economic Area. The research reported upon contributes to awareness of the importance of understanding both the legislative framework and technical practices involved in identifying the time of signing for ensuring the legal validity and reliability of electronic signatures.