Bookkeeping and accounting is a prevalent feature of small organizations, which has changed face quite substantially with the advent of personal computers and, later, the Internet. The emergence of digitalized accounting procedures has taken place in a nexus of different types of actors (e.g., software developers, accountancy firms and the businesses themselves), regulatory frameworks (e.g., bookkeeping laws and accounting standards) and technical frameworks (e.g., standards for software interactions with banks and tax authorities). Altogether, this has made the paths taken in this process to be largely national. In general, this process of digitalization is largely undocumented and untheorized in research despite its profound impact on practice. Against this backdrop, this chapter has a descriptive and forward-looking approach, documenting the case of how Swedish bookkeeping practices of small organizations became digitalized, which can work as a reference case for comparisons with other national contexts.