Can reproduce:

from typing import Literal


T = Literal['first', 'second']
v: T

v = ''

2024-05-09 18:34:12,233 [ 820111]   FINE - #c.i.p.l.i.c.Lsp4jServerConnector - --> PyrightLSDescriptor@project:
{
    "jsonrpc": "2.0",
    "id": "61",
    "method": "textDocument/completion",
    "params": {
        "context": { "triggerKind": 1 },
        "textDocument": { "uri": "file:///<project>/.py" },
        "position": { "line": 6, "character": 5 }
    }
}
2024-05-09 18:34:12,235 [ 820113]   FINE - #c.i.p.l.i.c.Lsp4jServerConnector - <-- PyrightLSDescriptor@project:
{
    "jsonrpc": "2.0",
    "id": "61",
    "result": {
        "items": [
            ...,
            {
                "label": "'second'", "kind": 21, "sortText": "03.9999.'second'",
                "textEdit": {
                    "range": {
                        "start": { "line": 6, "character": 4 },
                        "end": { "line": 6, "character": 6 }
                    },
                    "newText": "'second'"
                }
            }
        ],
        "isIncomplete": true
    }
}
2024-05-09 18:34:12,724 [ 820602]   FINE - #c.i.p.l.i.c.Lsp4jServerConnector - --> PyrightLSDescriptor@project:
{
    "jsonrpc": "2.0",
    "method": "textDocument/didChange",
    "params": {
        "textDocument": { "version": 48, "uri": "file:///<project>/.py" },
        "contentChanges": [
            {
                "range": {
                    "start": { "line": 6, "character": 5 },
                    "end": { "line": 6, "character": 5 }
                },
                "text": "second'"
            }
        ]
    }
}

I believe this is not a problem with the plugin (I overrode none of the default behaviours, as you can see here), but a problem with how PyCharm interprets the suggestions.

The first request was triggered by pressing Ctrl Space in the middle of the two quotes:

{
    "method": "textDocument/completion",
    "params": {
        // | 0 | 1 | 2 | 3 | 4 | 5 | 6 |
        // | v |   | = |   | ' | ' |
        "position": { "line": 6, "character": 5 }
    }
}

The corresponding response then gave back two items, both of which have the same textEdit range spanning from character 4 up to 6 (which presumably means both quotes are replaced) and a newText value having both leading and trailing quotes:

{
    "result": {
        "items": [
            ...,
            {
                "label": "'second'",
                "textEdit": {
                    "range": {
                        // | 0 | 1 | 2 | 3 | 4 | 5 | 6 |
                        // | v |   | = |   | ' | ' |
                        "start": { "line": 6, "character": 4 },
                        "end": { "line": 6, "character": 6 }
                    },
                    "newText": "'second'"
                }
            }
        ],
        "isIncomplete": true
    }
}

On accept, PyCharm sent this request, telling that it added second' (with no leading quote but one trailing) at (the position right before) character 5, leaving the trailing quote intact:

{
    "method": "textDocument/didChange",
    "params": {
        "contentChanges": [
            {
                "range": {
                    // | 0 | 1 | 2 | 3 | 4 | 5 | 6 |
                    // | v |   | = |   | ' | ' |
                    // =====================================================
                    // | 0 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 0 | 1 | 2 |
                    // | v |   | = |   | ' | s | e | c | o | n | d | ' | ' |
                    "start": { "line": 6, "character": 5 },
                    "end": { "line": 6, "character": 5 }
                },
                "text": "second'"
            }
        ]
    }
}

I'll see what I can do.

Progress update: I'm stuck. The best I can do for now is monkeypatching.

Setup:

from typing import Literal, TypedDict

class D(TypedDict):
	first: int
	second: str

v: Literal['first', 'second']
d: D

v = '|'
v = '''|'''
d = {'|': ''}
d = {'''|''': ''}

Default behavior:

v = 'first'|'
v = '''first'|'''
d = {'second'|': ''}
d = {'''second'|''': ''}

Desired behaviour:

v = 'first'|
v = '''first'''|
d = {'second'|: ''}
d = {'''second'''|: ''}

Monkeypatched behaviour, version 1 (remove the trailing quote for this one case, fallback to default):

v = 'first|'
v = '''first|'''
d = {'second|': ''}
d = {'''second|''': ''}

Monkeypatched behaviour, version 2 (override default entirely: replace the range with replacement, then put caret at the end of replacement):

v = 'first'|
v = '''first'|''
d = {'second'|: ''}
d = {'''second'|'': ''}

Both are nowhere near my expectations. Regardless, I'm pushing them for review.

It turns out PyCharm's behaviour is the same as monkeypatch 1 (no completions for Literals):

d = {'second|': ''}
d = {'''second|''': ''}

...and VSCode's is the same as monkeypatch 2:

v = 'first'|
v = '''first'|''
d = {'second'|: ''}
d = {'''second'|'': ''}

Still, it doesn't change the fact that I consider both of these subpar. This calls for an upstream issue.

I would still appreciate if you could align it with pycharms behavior for now. The Jet brains teams takes ages to fix something

@johannesschaffer #52 it is, then. Could you install the fix and play with it for some time first? I already did some testing on my own, but natural workflows tend to be better bug finders.

Sorry, I don't know how to install a plugin other than via the marketplace

See the README. The workflow to choose is the one linked from the PR.