Our Gemara on Amud Aleph discusses a situation where Rabbi Meir made a halakhic ruling, but then was confronted in a dream that he was an error. He stuck to his original logical analysis, and disregarded his dream:
הָהוּא אַפּוֹטְרוֹפּוֹס דַּהֲוָה בְּשִׁבָבוּתֵיהּ דְּרַבִּי מֵאִיר, דַּהֲוָה קָא מְזַבֵּין אַרְעָתָא וְזָבֵין עַבְדֵי, וְלָא שַׁבְקֵיהּ רַבִּי מֵאִיר. אַחְווֹ לֵיהּ בְּחֶלְמֵיהּ ״אֲנִי לַהֲרוֹס וְאַתָּה לִבְנוֹת?!״ אֲפִילּוּ הָכִי לָא אַשְׁגַּח, אֲמַר: דִּבְרֵי חֲלוֹמוֹת לֹא מַעֲלִין וְלֹא מוֹרִידִין.
It is related that there was a certain steward who was in Rabbi Meir’s neighborhood who was selling land belonging to the orphans and purchasing slaves with the proceeds, and Rabbi Meir did not allow him to do this, as the practice is contrary to halakha. They showed him in his dream the words: I wish to destroy and you build? He understood this as a sign that God wanted the orphans to suffer financial collapse, and therefore it would be preferable to allow the steward to continue his practice. Even so, Rabbi Meir paid no heed to his dream, and said: Words appearing in dreams do not bring up and do not take down; they should not be taken into consideration. (Bava Metzia 86b)
It is a fascinating topic of discussion how sometimes in Rabbinic literature dreams are taken as ominous portents and other times not taken seriously. Aside from our Gemara we have other incidents in the Talmud where financial obligations were not impacted, regardless of how powerful the evidence is from a dream. In fact, it is codified in Shulkhan Arukh (CM 55:9) that even if one has a dream telling him where, in certain amount of money is hidden from his father‘s estate, and it actually is an unpaid debt, even if the location and the amount turns out to be uncannily accurate, he has no obligation legally to turn this money over to whom ever the dream said it is owed.
On the other hand, in Gemara Nedarim (8b), oaths and excommunications that occur during dreams are to be taken as valid. This suggests that certain types of dreams hold significance and are treated as credible sources of information. The Torah Temimah (Bereishis 37:9) explains that dreams often reflect a person's preoccupations and thoughts during the day. Therefore, if someone is genuinely concerned about an oath or the possibility of being excommunicated, their dream relating to these matters is given weight and considered seriously. That is, his spiritual concerns while possibly not totally accurate, have significance. However, in regard to monetary matters, there can be enough inaccuracies to suspend obligation. (Note: This is my interpretation of the Torah Temimah. It is ambiguous so check it out yourself and draw your own conclusions.)
The idea of dreams being prophetic and their intersection with our unconscious imaginative faculty encompasses a complex spiritual, theological, and psychological interaction. Maimonides, in his work "Guide for the Perplexed" (II:41), delves into this topic, acknowledging the intricate nature of dreams and their potential prophetic qualities employing aspects of human imagination as it encounters divine stimuli.
This symbolic, non-cognitive part of ourselves possesses an astounding capacity for attunement and recognition of vast patterns and data. It can manifest in the conscious mind through symbols, imagery, or sudden thoughts. This aligns with the teachings of the Talmud (Berakhos 57b), where Rabbi Yoḥanan states that if a person wakes up in the morning with a verse on their lips, it is considered a minor form of prophecy. Additionally, the Talmud suggests that a dream is 1/60th of prophecy, highlighting the potential significance of dreams as sources of divine communication.
The phenomenon of prophetic experiences extends beyond the Gemara. Many great Rabbis throughout the Middle Ages spoke of experiencing Ruach Hakodesh, divine inspiration. For instance, Rav Yosef Karo, the author of the Shulkhan Arukh, documented his encounters with a personal maggid, an entity that appeared to him and conveyed teachings. His Sefer, called Magid Mesharim, provides insights into the divine teachings he received.
An intriguing aspect related to the reliability of these revelations is a conversation between Rabbi Kloft and the Chazon Ish, as recounted by Tzvi Yabrov (Maase Ish, 1998, pp. 119, 187). Rabbi Kloft questioned whether Rav Karo's halakhic rulings in Magid Mesharim, which originated from supernatural sources, should be exclusively followed. The Chazon Ish responded, "Rav Karo's Magid is also Rav Karo," implying that the authority of Rav Karo's Maggidic rulings carries no more weight than Rav Karo himself.
This statement requires nuanced understanding. The Maggid was a manifestation of a spiritual resource within Rav Karo, suggesting that his prophetic experiences were not mere figments of imagination. To further illustrate this concept, we can consider an opinion presented by Tosafos (Shabbos 87a, Yevamos 62a) regarding Miriam's and Aharon's criticism of Moses' celibacy and separation from his wife. Tosafos suggests that Moses initially made the decision to separate based on his own judgment, and later God endorsed his choice. Miriam and Aharon objected due to the principle that "God leads a person in accordance to his inclination." This principle is extended even to Moshe's prophetic permission to separate from his wife. However, this subjective aspect of Moshe's personal prophecy does not diminish his role as the eternal lawgiver and authoritative prophet when giving prophecy to the Jewish people.
Therefore, we can interpret these instances as instances where individuals communicate or perceive divine will through their own delving into the sense of God within self, decoding God's message from within themselves. While subjective in nature, they nonetheless bear divine significance.
Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation 
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