Woltemade's departure came in the final stages of the transfer window, with Newcastle United looking to facilitate a £51million move for Matias Fernandez-Pardo. The striker's removal from the wage bill also helped the club manage their finances under the Premier League's squad cost rules.
His exit was particularly complicated because Woltemade had initially asked Jaissle for the opportunity to fight for his place at Newcastle. The forward was subsequently told that he did not fit the manager's preferred system, prompting his loan move to Italy.
However, sources close to the player have indicated that Jaissle has remained in regular contact with Woltemade in recent weeks, offering encouragement and reminding him that the door has not been closed on a return to Newcastle.
That message is significant given the circumstances of the 6ft 6in striker's departure. While he is currently concentrating on establishing himself at Juventus, there remains a possibility that he could return to England in the summer.
Jaissle had already addressed Woltemade's situation in an interview with Kicker last month, explaining the thinking behind the decision to allow him to leave while stressing the high regard in which he holds the player.
"We communicated very clearly where he stood within the team at that moment, particularly considering the way we play football with high pressing. At the time, one or two other players were simply a little ahead of him.
"Open discussions are important regardless of whether someone is your compatriot or not. But I rate him very highly, and of course he remains our player because he's only out on loan."
Those comments underline that Newcastle have not necessarily given up on Woltemade, even if the tactical considerations that prompted his departure remain relevant.
The striker has shown signs of finding his feet in Italy, scoring three goals in the Europa League and receiving Juventus' MVP award for October. He also ended his Serie A goal drought with a first-half strike in the 2-2 draw against Fiorentina, taking his overall tally for the club to four goals in all competitions.
Woltemade swept home from Kolo Muani's cross in the 32nd minute, although he was substituted shortly after the hour mark as Luciano Spalletti looked to change his team's approach. Gleison Bremer eventually rescued a point for Juventus with a second-half header.
His performances have reportedly left him baffled by his omission from the Germany squad for the Nations League fixtures against Serbia and the Netherlands, particularly given his recent contributions in European competition.
The international break now provides Woltemade with a pause before he returns to Juventus duties, but the bigger question concerns what happens when his loan spell ends.
Newcastle's decision to sanction his departure was driven by a combination of tactical and financial considerations, rather than necessarily representing a permanent end to his time at the club.
Jaissle's continued communication with the striker suggests that Newcastle are still monitoring his progress and that a future return has not been ruled out. Whether Woltemade can eventually convince the manager that he can fit into his plans remains to be seen, but the relationship has clearly not been abandoned.