The ability to react to events in the external world determines the fate of every living organism, this general state of readiness is called as ’alertness’. What happens to neurodynamics in the brain when alertness fades away as we fall asleep? How is behaviour affected? These questions will help us understand the organizing principles in the brain and functions of sleep itself. Here I use two distant animal models, the richness in behaviour and complexity of the human brain to understand how alertness transitions affects attention; and the experimental flexibility of the fruit fly, to understand its effect over longer time intervals. I first develop an objective method to track alertness using Electroencephalography (EEG). Then, I investigate the behavioural dynamics using an auditory spatial attention task while participants fall asleep. By using multilevel modelling and psychophysics, I show that participants systematically misclassify tones from the left side when drowsy, and further with a hierarchical drift diffusion model (HDDM) show how drift-rate (evidence accumulation) explains errors. Then, I show convergent evidence in the neural dynamics using multivariate pattern analysis (MVPA). Next, I probe the effect of handedness on the same task. Handedness affects behaviour only under drowsy condition and I show how neural dynamics are affected by a combination of handedness and alertness. To approach alertness transitions in a system with reduced neural complexity, I explore those dynamics in the fruit fly (Drosophila melanogaster), using both single and multichannel local field potential (LFP) data to show how alertness transitions and sleep modulate different regions of the fly brain. Further, I validate the results by converging evidence from causal manipulations. Finally, I discuss how the mapping of alertness transitions -under natural conditions- can help us understand fundamental questions in neuroscience such as the functions of sleep or the mechanisms of general anaesthesia.