Gnucash
I'm a big fan of FOSS software in general. One of my favourites and most used pieces of software is Gnucash. I've been using Gnucash to manage my personal finances for years. It's reasonably simple to understand how it operates. I've not read the documentation, but have been able to figure most of it out.
My workflow usually consists of me entering cash data onto the Android app and importing that data and bank statement data into the desktop app. I can then allocate funds accuratley and quickly. Gnucash is able to associate descriptions from your bank statements with Gnucash categories to speed things up. Great if one description always matches up with the correct category. Not so much if the description has different categories.
My main area of criticism with Gnucash is the reporting. However, reporting across the board on accounting products is weak. Wether that's accountants like thier own reports, or are protecting their jobs by writing their own Excel reports - I'm not sure. The reports are passable, however, a report I'd really like is a time series cashflow. Gnucash can produce a total for a period, but not a time series, so I have to enter the data onto a spreadsheet - classic accountant. I'm sure I could write the report I want for Gnucash (it's FOSS after all), but I don't have the intellectual capacity, nor the programming skills at this time.
It's also not got a web front end, and the mysql database is experiental. Which means it's not great if you want multiple logins, or to use different machines, or use a server.
Still, for personal finance, where you are the only user, it's great. I've look around and have nto found anything that is close to this comprehensive without being overwhelming and non-free.