This paper analyses relevant courts' decisions across Canada when determining whether the length of time an immigration detainee has become illegal by way of habeas corpus. Prison conditions are not suitable for immigration detainees, and violations of detainee’s rights are rife – thus the lengthy detention of immigration detainees exposes them to horrific conditions of care in custody. Detainees have taken to Canadian courts to challenge, by way of habeas corpus, the length of their detention and the uncertainty regarding the date of release. The courts have held differently on the duration of detention considered to be too lengthy – in one case, 17 months was ruled as unduly lengthy, yet in another case, four and a half years was adjudged as being insufficient for a habeas corpus relief. This paper reviews the reasonings in Ontario Courts’ decision in R v Ogiamen (2016), Canada v Dadzie (2016), Ali v Canada (2017), and Scotland v Canada (2017) regarding the length and uncertainty of detention that qualify for a habeas corpus relief.