Although Ivan Shishman has been categorized as indecisive and inconsistent in his policy in the past, this was done with little regard for an understanding of the context of the conditions and limited resources that this ruler had at his disposal.

Two years later, Sultan Bayezid I captured Nicopolis with a surprise approach from the north of the fortress after two failed campaigns in Hungary and Wallachia, summoning Ivan Shishman on the false pretense of a discussion and had him executed by beheading.

Despite the military and political weakness, during his rule Bulgaria remained a major cultural center and the ideas of Hesychasm dominated the Bulgarian Orthodox Church.

[14][15] Only a few months after the ascension of Ivan Shishman to the throne, on 26 September 1371, the Ottoman Turks defeated a large Christian army led by the Serbian brothers Vukašin of Serbia and Uglješa Mrnjavčević in the Battle of Maritsa.

[17] Ottoman sultan Murad I forced Ivan Shishman to retreat to the north of the Balkan Mountains and conquered northern Thrace, the Rhodopes, Kostenets, Ihtiman and Samokov.

[18] Under this agreement, Bulgaria regained some of the conquered territories such as Ihtiman and Samokov and began nearly ten years of uneasy peace with the Turks.

[10][19] Despite the vassalage and the peace treaty, Ottoman raids were renewed in the beginning of the 1380s and culminated in 1385 with the fall of Sofia, the last stronghold of Ivan Shishman to the south of the Balkan Mountains.

Encouraged by the Christian success, Ivan Shishman immediately invalidated his vassalage to Murad I and refused to send troops in his support in 1388.

[24][25] However, Ivan Shishman, reassured by his neighbours that he would receive support and the preparations of Serbia for war, not only refused to let the Ottomans in the city but also strengthened its walls.

[26] Ali Pasha crossed the Balkan Mountains for a second time to consecutively capture Shumen, Cherven, Svishtov and once again besiege Ivan Shishman in Nikopol.

His pleas were accepted, but the terms were harsher than the original: not only Silistra was to be surrendered, but Ottoman garrisons were to be stationed in other Bulgarian cities, most notably Shumen and Ovech.

[33] Upon his return from Wallachia after the Battle of Rovine in 1395, Bayezid I attacked and captured Nikopol and, according to the Anonymous Bulgarian Chronicle, murdered Ivan Shishman on 3 June 1395.

[39][40] Evtimiy wrote a number of religious works, including hagiographies, praises and letters, but is most famous with the orthographic reform and the standardization of the Bulgarian language, which had an impact in Serbia, Wallachia and the Russian principalities.

[38] Evtimiy thought that many of the scholars were not sufficiently prepared, and that the translations of Greek texts in local dialects and peculiarities could lead to misinterpretation of the original and eventually to heretism.

The texts regarding the reform did not survive, although its character has been partly recreated by the historians and linguists by analyzing the works of Evtimiy himself and his disciples.

The orthography was inspired by the original Old Church Slavonic during the heyday of the First Bulgarian Empire;[38] the reform also included syntax changes and enrichment of the lexicon with a number of synonyms to avoid repetition.

Наистина блажен съм аз сред градовете, защото добри съкровища събрах - честитите мощи на светците, чието застъпничество като притежавам, от всякакви злини се избавям.

[43] Evtimiy was an active opponent to heresies, but it appears that since the mid-14th century the influence of the Bogomils, the most prominent heretic movement in the Balkans at the time, had been greatly reduced in Bulgaria and no document mentions them after 1360.

[46] Some of the most prominent Bulgarian émigrés included Constantine of Kostenets, who worked in Serbia, and Cyprian, Metropolitan of Kiev and Gregory Tsamblak in the Russian lands.

After the death of Ivan Alexander and the breakaway of Dobrotitsa's Principality of Karvuna, Tarnovo also lost its most important port Varna, leading to a reduction in commerce and tax revenues.

[50] He is often viewed as having intruded onto the throne due to the intrigues of his mother and thus taking the place of the rightful successor, his elder brother Ivan Sratsimir.

That legendary "geography" is mainly concentrated in the region of Sofia, Ihtiman and Samokov,[60][61] though it extends to the Rhodope Mountains, Sredna Gora, Vratsa, Pleven, Prilep, Varna, etc.

[59] Other related toponyms usually associated with the emperor's last stand are Kokalyane (derived from kokal, meaning "bone"), Cherepish (from cherep, "skull") and Lyutibrod ("Fierce Ford"),[59] all thought to be hinting at the fate of the perished Bulgarian troops.

[65] He is also said to have fought in the Balkan Mountains at Shishkin grad ("Shishman's town"), between Sliven and Kazanlak, where he killed 10,000 janissaries in a huge battle.

[61] The 18th century Bulgarian enlightener[c] Paisius of Hilendar wrote in his Istoriya Slavyanobolgarskaya that during the siege of Tarnovo Ivan Shishman managed to reach Sofia with his boyars.

[61] Some versions suggest that Kokalyanski Urvich remained the last fortress to fall and before Shishman died he buried treasure under the castle and tried to escape by cutting a passage through the mountain.

[60] The repeating motif of the treasure is a sacral symbol of the Bulgarian statehood and the usual locations of the imperial jewellery are monasteries, lakes or hideouts under rivers.

In a song from the region of Sliven, the death of the emperor brings chaos to nature and rivers of "black blood" (typical folklore collocation) start flowing.

[66] The people desired to berhyme the image of the "ideal emperor", a defender and protector, whose strength they needed to survive under Ottoman domination, and not the actual historical personality.