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Most devils have the feature Devil's Sight:

Devil's Sight. Magical darkness doesn't impede the [devil's] darkvision.

The Gloom Stalker's Umbral Sight says:

…You are also adept at evading creatures that rely on darkvision. While in darkness, you are invisible to any creature that relies on darkvision to see you in that darkness.

By my interpretation, the Gloom Stalker will remain hidden, even from a devil, when in darkness; however, my DM believes the devil will be able to see the Gloom Stalker with just their darkvision, as the effect is magical.

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Umbral Sight's invisibility is neither magical nor darkness.

Nothing in the description of the Umbral Sight feature indicates that it is considered magical. In fact, the description strongly implies the opposite, by saying that your invisibility is a consequence of being "adept at evading creatures that rely on darkvision".

However, even if your DM rules that Umbral Sight is considered magical, the invisibility from the feature is not "magical darkness". Magical darkness would be something like the effect of a darkness spell -- specifically, an area of darkness created by magic. Umbral Sight does not create any kind of darkness, magical or otherwise -- instead, it takes advantage of existing darkness, granting invisibility. Nothing about Devil's Sight allows a creature to see invisible creatures.

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  • \$\begingroup\$ Small addition how I'd rule a niceh case: IF the darkness that triggers Umbral sight (as you have to be in darkness for it to take effect) is magical, I'd still rule it to work, since it's still darkvision at work \$\endgroup\$ – Hobbamok Dec 31 '20 at 14:23
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    \$\begingroup\$ This is true for a Devil's ability, but the Warlock's Devil's Sight Invocation is NOT worded as a modifier. They just gain the ability to see in darkness (with no mention of gaining darkvision). \$\endgroup\$ – Glasses2C_Sharp Dec 31 '20 at 17:08
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    \$\begingroup\$ @Hobbamok I'd disagree, darkvision turns dark into dim and dim into light, similar to darkvision goggles in the real world. Their vision is still okay but not necesarily as good as it is in bright daylight. The Devil's Sight feature on the other hand states that darkness does not impede vision which I read as there essentially being no darkness in the frame of the devil. \$\endgroup\$ – Martin - Reinstate Monica Dec 31 '20 at 18:19
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    \$\begingroup\$ @MartinvanIJcken disagree. (Non-Warlock) Devil's Sight says "Magical darkness doesn't impede the devil's darkvision." They still "rely on darkvision" to see in magical darkness. If the ability said vision instead of darkvision, then umbral sight would not apply. In either case, the darkness still exists for any purpose other than vision. If some effect specified "while in darkness, X happens", then X would still happen to a devil, because that wording doesn't care about vision, it cares about physical location. \$\endgroup\$ – Foo Bar Jan 4 at 12:02
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Devil’s Sight

You can see normally in darkness, both magical and nonmagical, to a distance of 120 feet.

Umbral Sight

At 3rd level, you gain darkvision out to a range of 60 feet. If you already have darkvision from your race, its range increases by 30 feet.

You are also adept at evading creatures that rely on darkvision. While in darkness, you are invisible to any creature that relies on darkvision to see you in that darkness.

You see normally in darkness with Devil's Sight. You do NOT rely on darkvision to see in darkness. Umbral Sight grants invisibility to you against any creature that relies on darkvision to see you in that darkness.

No darkvision is being used to see the Gloom Stalker. Umbral Sight does NOT apply, because darkvision is NOT being used.

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  • \$\begingroup\$ The Devil's Sight feature you have quoted is a Warlock Eldritch Invocation, which is worded differently from a Devil's Devil's Sight feature such as the Chain Devil's. Compare "You can see normally in darkness, both magical and nonmagical, to a distance of 120 feet." with "Magical darkness doesn't impede the devil's darkvision." The question was about the latter feature while you addressed the former, thus, at least technically, this does not actually answer the question \$\endgroup\$ – Medix2 Feb 21 at 23:53
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    \$\begingroup\$ It looks like you've accidentally made two accounts. You should go through the process of getting them merged so that you own your own answer and should be able to delete it if desired (if not, please raise a flag). \$\endgroup\$ – Someone_Evil Feb 22 at 12:30

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