Dermoscopy has been documented to increase the diagnostic accuracy of clinicians evaluating skin tumours, improving their ability to detect skin cancer and better recognize benign moles. However, dermoscopically 'false-positive' and 'false-negative' tumours do exist. False-positive diagnosis usually leads to unnecessary excisions. False-negative diagnosis is much more dangerous, as it might result in overlooking a cancer, with severe undesirable consequences for the patient and the physician. Therefore, management strategies should mainly focus on addressing the risk of dermoscopically false-negative tumours. The most frequent benign tumours that might acquire dermatoscopic characteristics suggestive of malignancy are seborrhoeic keratosis (SK), including solar lentigo, melanoacanthoma, irritated, clonal and regressive SK, angioma (mainly thrombosed angioma and angiokeratoma), dermatofibroma, benign adnexal tumours and naevi (Clark, Spitz, recurrent, combined, sclerosing). The most useful clues to recognize these tumours are the following: solar lentigo - broad network; melanoacanthoma - sharp border; irritated SK - regularly distributed white perivascular halos; clonal SK - classic SK criteria; regressive SK - remnants of SK; targetoid haemosiderotic haemangioma - dark centre and reddish periphery; thrombosed angioma - sharp demarcation; angiokeratoma - dark lacunae; atypical dermatofibromas - palpation; follicular tumours - white colour; sebaceous tumours - yellow colour; Clark naevi - clinical context; Spitz/Reed naevi - age; combined naevi - blue central area; recurrent naevi - pigmentation within the scar; sclerosing naevi - age and location on the upper back; blue naevi - history. Malignant tumours that might mimic benign ones and escape detection are melanoma (in situ, nevoid, spitzoid, verrucous, regressive, amelanotic), squamous cell carcinoma (mainly well-differentiated variants) and rarely basal cell carcinoma (non-pigmented variants). The most useful clues to recognize the peculiar melanoma subtypes are as follows: melanoma in situ - irregular hyperpigmented areas; nevoid melanoma - history of growth; spitzoid melanoma - age; verrucous melanoma - blue-black sign; regressive melanoma - peppering or scar-like depigmentation; amelanotic melanoma - pink colour, linear irregular vessels, dotted vessels. In this article, we summarized the most frequent dermoscopic variations of common skin tumours that are often misinterpreted, aiming to assist clinicians to reduce the number of false diagnoses.