Climate is one of the key drivers of the plant community’s structure and trends. However, the regional vegetation-climate features in the ecotone have not yet been sufficiently studied. The aim of the research is to study features of Pinus sibirica Du Tour germination, survival, and growth in the mountain tundra of the Northern Urals against the background of a changing climate. The following research objectives were set: To determine the abundance and age structure of P. sibirica undergrowth on the mountain tundra plateau, identify the features of P. sibirica growth in the mountain tundra, and examine the correlation between the multi-year air temperature pattern, precipitation, and P. sibirica seedling emergence. A detailed study of the Pinus sibirica natural regeneration in the mountain stony shrub-moss-lichen tundra area at an altitude of 1010–1040 m above sea level on the Tri Bugra mountain massif plateau (59°30′ N, 59°15′ E) in the Northern Urals (Russia) has been conducted. The research involved the period between 1965 and 2017. Woody plant undergrowth was considered in 30 plots, 5 × 5 m in size. The first generations were recorded from 1967–1969. The regeneration has become regular since 1978 and its intensity has been increasing since then. Climate warming is driving these processes. Correlation analysis revealed significant relationships between the number of Pinus sibirica seedlings and the minimum temperature in August and September of the current year, the minimum temperatures in May, June, and November of the previous year, the maximum temperatures in May and August of the current year, and precipitation in March of both the current and previous years. However, the young tree growth rate remains low to date (the height at an age of 45–50 years is approximately 114 ± 8.8 cm). At the same time, its open crowns are rare single lateral shoots. The length of the side shoots exceeds its height by 4–5 times, and the length of the lateral roots exceeds its height by 1.2–1.5 times. This is an indicator of the extreme conditions for this tree species. With the current rates of climate warming and the Pinus sibirica tree growth trends, the revealed relationships allow for the prediction that in 20–25 years, the mountain tundra in the studied Northern Urals plateau could develop underground-closed forest communities with a certain forest relationship. The research results are of theoretical importance for clarifying the forest-tundra ecotone concept. From a practical point of view, the revealed relationship can be used to predict the trend in forest ecosystem formation in the mountain forest-tundra ecotone.