Does repentance halakhically depend on a verbal itemization in confession, or is it sufficient to simply confess that one has sinned? This is subject to a debate in Yoma (86b) between Rabbi Yehuda ben Bava and Rabbi Akiva. Rabbi Akiva holds that it is sufficient to confess sin in general, without specifying each trespass. 

Our Gemara on Amud Beis states a general rule regarding halakha and Rabbi Akiva. The halakha is in accordance with Rabbi Akiva when arguing with a colleague. If so, presumably one is not required to make an itemized confession. Yet, in practice we see that we do itemize confessions such as in the Al-Chet liturgy. The Rambam (Laws of Repentance 2:3) also rules that one must specify his sins as part of the viduy confession. The commentaries on the Rambam try to resolve why he ruled like Rabbi Yeguda ben Bava and did not follow the standard rule in accordance with Rabbi Akiva. Some say, the Gemara later favors Rabbi Yehuda ben Bava’s position by asking and resolving scriptural concerns related to his position. Others try to answer that since Rabbi Yehuda was from a prior generation, he is not a peer of Rabbi Akiva’s but considered a teacher, and not subject to the rule. And one final opinion holds that even Rabbi Akiva only meant that one is not required to specify sins publicly, but in his or her private confession, one is required to enumerate his sins.

Sometimes small halakhic debates can have an enormous impact. I think observance of repentance would be radically different without specifying sins. The impact on consciousness that being open and honest with self by having to enumerate one’s sins seems to be dramatically different than merely acknowledging sin. It makes you wonder how Rabbi Akiva’s position is logically and theologically tenable. The easiest answer is that Rabbi Akiva was not discussing the optimal, but rather the bare minimum. Yet, this is not borne out by the scriptural proof he offers in Yoma:

לְדָוִ֗ד מַ֫שְׂכִּ֥יל אַשְׁרֵ֥י נְֽשׂוּי־פֶּ֗שַׁע כְּס֣וּי חֲטָאָֽה׃

Of David. A maskil. Happy is he whose transgression is forgiven,whose sin is covered over. (Psalm 32:1).

This seems to be an unqualified approbation of not specifying sin in confession! 

Zohar (III:101a) seems to hold that this verse is also only referring to public confession, perhaps to say that one is fortunate if his sins are forgiven and he had not publicly violated or shown a violation. The verse is then saying, fortunate is one who catches his sin early, repents and does not cause public desecration. This interpretation is inline with one of the explanations we saw above regarding Rabbi Akiva, that only public specification of sin is not required.

The Zohar (ibid) also suggests that one may merit a status where God covers up the sin, so to speak. I believe the Zohar is expressing an idea that a person can be granted forgiveness even when technically, the correction or restitution was not fully made. This brings to mind something I noticed in the Avinu Malkenu liturgy. We ask to be written in the Scroll of Forgiveness. It is an odd prayer. I would think that we are praying for success and to be judged favorably, and part of that involves repentance and forgiveness. Forgiveness is more of a means to an end than a specific outcome to pray for. However, we can say the answers is that forgiveness itself is something to pray for and can be granted, even when the process of repentance is not performed with full restoration and correction.