diff --git a/crates/assists/src/handlers/merge_imports.rs b/crates/assists/src/handlers/merge_imports.rs
index 0bd6792605..fe33cee53c 100644
--- a/crates/assists/src/handlers/merge_imports.rs
+++ b/crates/assists/src/handlers/merge_imports.rs
@@ -95,7 +95,7 @@ use std::fmt::Debug;
 use std::fmt<|>::Display;
 ",
             r"
-use std::fmt::{Display, Debug};
+use std::fmt::{Debug, Display};
 ",
         );
     }
@@ -122,7 +122,7 @@ use std::fmt::{self, Display};
 use std::{fmt, <|>fmt::Display};
 ",
             r"
-use std::{fmt::{Display, self}};
+use std::{fmt::{self, Display}};
 ",
         );
     }
@@ -210,13 +210,17 @@ use std::{fmt<|>::Debug, fmt::Display};
 use std::{fmt::{Debug, Display}};
 ",
         );
+    }
+
+    #[test]
+    fn test_merge_nested2() {
         check_assist(
             merge_imports,
             r"
 use std::{fmt::Debug, fmt<|>::Display};
 ",
             r"
-use std::{fmt::{Display, Debug}};
+use std::{fmt::{Debug, Display}};
 ",
         );
     }
@@ -310,9 +314,7 @@ use foo::<|>{
 };
 ",
             r"
-use foo::{
-    FooBar,
-bar::baz};
+use foo::{FooBar, bar::baz};
 ",
         )
     }
diff --git a/crates/assists/src/handlers/replace_qualified_name_with_use.rs b/crates/assists/src/handlers/replace_qualified_name_with_use.rs
index 85c70d16b6..093c3b101d 100644
--- a/crates/assists/src/handlers/replace_qualified_name_with_use.rs
+++ b/crates/assists/src/handlers/replace_qualified_name_with_use.rs
@@ -312,7 +312,7 @@ impl std::fmt<|> for Foo {
 }
     ",
             r"
-use std::fmt::{Debug, self};
+use std::fmt::{self, Debug};
 
 impl fmt for Foo {
 }
@@ -330,9 +330,8 @@ use std::fmt::{Debug, nested::{Display}};
 impl std::fmt::nested<|> for Foo {
 }
 ",
-            // FIXME(veykril): should be nested::{self, Display} here
             r"
-use std::fmt::{Debug, nested::{Display}, nested};
+use std::fmt::{Debug, nested::{self, Display}};
 
 impl nested for Foo {
 }
@@ -350,9 +349,8 @@ use std::fmt::{Debug, nested::{self, Display}};
 impl std::fmt::nested<|> for Foo {
 }
 ",
-            // FIXME(veykril): nested is duplicated now
             r"
-use std::fmt::{Debug, nested::{self, Display}, nested};
+use std::fmt::{Debug, nested::{self, Display}};
 
 impl nested for Foo {
 }
@@ -371,7 +369,7 @@ impl std::fmt::nested::Debug<|> for Foo {
 }
 ",
             r"
-use std::fmt::{Debug, nested::{Display}, nested::Debug};
+use std::fmt::{Debug, nested::{Debug, Display}};
 
 impl Debug for Foo {
 }
@@ -409,7 +407,7 @@ impl std::fmt::Display<|> for Foo {
 }
 ",
             r"
-use std::fmt::{nested::Debug, Display};
+use std::fmt::{Display, nested::Debug};
 
 impl Display for Foo {
 }
@@ -429,12 +427,8 @@ use crate::{
 
 fn foo() { crate::ty::lower<|>::trait_env() }
 ",
-            // FIXME(veykril): formatting broke here
             r"
-use crate::{
-    ty::{Substs, Ty},
-    AssocItem,
-ty::lower};
+use crate::{AssocItem, ty::{Substs, Ty, lower}};
 
 fn foo() { lower::trait_env() }
 ",
@@ -633,7 +627,7 @@ fn main() {
 }
     ",
             r"
-use std::fmt::{Display, self};
+use std::fmt::{self, Display};
 
 fn main() {
     fmt;
diff --git a/crates/assists/src/utils/insert_use.rs b/crates/assists/src/utils/insert_use.rs
index 98553b2e08..4f5fd317a3 100644
--- a/crates/assists/src/utils/insert_use.rs
+++ b/crates/assists/src/utils/insert_use.rs
@@ -1,7 +1,9 @@
 //! Handle syntactic aspects of inserting a new `use`.
-use std::iter::{self, successors};
+use std::{
+    cmp::Ordering,
+    iter::{self, successors},
+};
 
-use algo::skip_trivia_token;
 use ast::{
     edit::{AstNodeEdit, IndentLevel},
     PathSegmentKind, VisibilityOwner,
@@ -9,9 +11,8 @@ use ast::{
 use syntax::{
     algo,
     ast::{self, make, AstNode},
-    Direction, InsertPosition, SyntaxElement, SyntaxNode, T,
+    InsertPosition, SyntaxElement, SyntaxNode,
 };
-use test_utils::mark;
 
 #[derive(Debug)]
 pub enum ImportScope {
@@ -163,18 +164,48 @@ pub(crate) fn try_merge_imports(
     Some(old.with_use_tree(merged))
 }
 
-/// Simple function that checks if a UseTreeList is deeper than one level
-fn use_tree_list_is_nested(tl: &ast::UseTreeList) -> bool {
-    tl.use_trees().any(|use_tree| {
-        use_tree.use_tree_list().is_some() || use_tree.path().and_then(|p| p.qualifier()).is_some()
-    })
+/// Orders paths in the following way:
+/// the sole self token comes first, after that come uppercase identifiers, then lowercase identifiers
+/// FIXME: rustfmt sort lowercase idents before uppercase
+fn path_cmp(a: &ast::Path, b: &ast::Path) -> Ordering {
+    let a = segment_iter(a);
+    let b = segment_iter(b);
+    let mut a_clone = a.clone();
+    let mut b_clone = b.clone();
+    match (
+        a_clone.next().and_then(|ps| ps.self_token()).is_some() && a_clone.next().is_none(),
+        b_clone.next().and_then(|ps| ps.self_token()).is_some() && b_clone.next().is_none(),
+    ) {
+        (true, true) => Ordering::Equal,
+        (true, false) => Ordering::Less,
+        (false, true) => Ordering::Greater,
+        (false, false) => {
+            // cmp_by would be useful for us here but that is currently unstable
+            // cmp doesnt work due the lifetimes on text's return type
+            a.zip(b)
+                .flat_map(|(seg, seg2)| seg.name_ref().zip(seg2.name_ref()))
+                .find_map(|(a, b)| match a.text().cmp(b.text()) {
+                    ord @ Ordering::Greater | ord @ Ordering::Less => Some(ord),
+                    Ordering::Equal => None,
+                })
+                .unwrap_or(Ordering::Equal)
+        }
+    }
+}
+
+fn path_cmp_opt(a: Option<ast::Path>, b: Option<ast::Path>) -> Ordering {
+    match (a, b) {
+        (None, None) => Ordering::Equal,
+        (None, Some(_)) => Ordering::Less,
+        (Some(_), None) => Ordering::Greater,
+        (Some(a), Some(b)) => path_cmp(&a, &b),
+    }
 }
 
-// FIXME: currently this merely prepends the new tree into old, ideally it would insert the items in a sorted fashion
 pub(crate) fn try_merge_trees(
     old: &ast::UseTree,
     new: &ast::UseTree,
-    merge_behaviour: MergeBehaviour,
+    merge: MergeBehaviour,
 ) -> Option<ast::UseTree> {
     let lhs_path = old.path()?;
     let rhs_path = new.path()?;
@@ -182,33 +213,89 @@ pub(crate) fn try_merge_trees(
     let (lhs_prefix, rhs_prefix) = common_prefix(&lhs_path, &rhs_path)?;
     let lhs = old.split_prefix(&lhs_prefix);
     let rhs = new.split_prefix(&rhs_prefix);
-    let lhs_tl = lhs.use_tree_list()?;
-    let rhs_tl = rhs.use_tree_list()?;
+    recursive_merge(&lhs, &rhs, merge).map(|(merged, _)| merged)
+}
 
-    // if we are only allowed to merge the last level check if the split off paths are only one level deep
-    if merge_behaviour == MergeBehaviour::Last
-        && (use_tree_list_is_nested(&lhs_tl) || use_tree_list_is_nested(&rhs_tl))
-    {
-        mark::hit!(test_last_merge_too_long);
-        return None;
-    }
+/// Returns the merged tree and the number of children it has, which is required to check if the tree is allowed to be used for MergeBehaviour::Last
+fn recursive_merge(
+    lhs: &ast::UseTree,
+    rhs: &ast::UseTree,
+    merge: MergeBehaviour,
+) -> Option<(ast::UseTree, usize)> {
+    let mut use_trees = lhs
+        .use_tree_list()
+        .into_iter()
+        .flat_map(|list| list.use_trees())
+        // check if any of the use trees are nested, if they are and the behaviour is last only we are not allowed to merge this
+        .map(|tree| match merge == MergeBehaviour::Last && tree.use_tree_list().is_some() {
+            true => None,
+            false => Some(tree),
+        })
+        .collect::<Option<Vec<_>>>()?;
+    use_trees.sort_unstable_by(|a, b| path_cmp_opt(a.path(), b.path()));
+    for rhs_t in rhs.use_tree_list().into_iter().flat_map(|list| list.use_trees()) {
+        let rhs_path = rhs_t.path();
+        match use_trees.binary_search_by(|p| path_cmp_opt(p.path(), rhs_path.clone())) {
+            Ok(idx) => {
+                let lhs_path = use_trees[idx].path()?;
+                let rhs_path = rhs_path?;
+                let (lhs_prefix, rhs_prefix) = common_prefix(&lhs_path, &rhs_path)?;
+                if lhs_prefix == lhs_path && rhs_prefix == rhs_path {
+                    let tree_is_self =
+                        |tree: ast::UseTree| tree.path().map(path_is_self).unwrap_or(false);
+                    // check if only one of the two trees has a tree list, and whether that then contains `self` or not.
+                    // If this is the case we can skip this iteration since the path without the list is already included in the other one via `self`
+                    if use_trees[idx]
+                        .use_tree_list()
+                        .xor(rhs_t.use_tree_list())
+                        .map(|tree_list| tree_list.use_trees().any(tree_is_self))
+                        .unwrap_or(false)
+                    {
+                        continue;
+                    }
 
-    let should_insert_comma = lhs_tl
-        .r_curly_token()
-        .and_then(|it| skip_trivia_token(it.prev_token()?, Direction::Prev))
-        .map(|it| it.kind())
-        != Some(T![,]);
-    let mut to_insert: Vec<SyntaxElement> = Vec::new();
-    if should_insert_comma {
-        to_insert.push(make::token(T![,]).into());
-        to_insert.push(make::tokens::single_space().into());
+                    // glob imports arent part of the use-tree lists so we need to special handle them here as well
+                    // this special handling is only required for when we merge a module import into a glob import of said module
+                    // see the `merge_self_glob` or `merge_mod_into_glob` tests
+                    if use_trees[idx].star_token().is_some() || rhs_t.star_token().is_some() {
+                        use_trees[idx] = make::use_tree(
+                            make::path_unqualified(make::path_segment_self()),
+                            None,
+                            None,
+                            false,
+                        );
+                        use_trees.insert(
+                            idx,
+                            make::use_tree(
+                                make::path_unqualified(make::path_segment_self()),
+                                None,
+                                None,
+                                true,
+                            ),
+                        );
+                        continue;
+                    }
+                }
+                let lhs = use_trees[idx].split_prefix(&lhs_prefix);
+                let rhs = rhs_t.split_prefix(&rhs_prefix);
+                match recursive_merge(&lhs, &rhs, merge) {
+                    Some((_, count))
+                        if merge == MergeBehaviour::Last && use_trees.len() > 1 && count > 1 =>
+                    {
+                        return None
+                    }
+                    Some((use_tree, _)) => use_trees[idx] = use_tree,
+                    None => use_trees.insert(idx, rhs_t),
+                }
+            }
+            Err(idx) => {
+                use_trees.insert(idx, rhs_t);
+            }
+        }
     }
-    to_insert.extend(
-        rhs_tl.syntax().children_with_tokens().filter(|it| !matches!(it.kind(), T!['{'] | T!['}'])),
-    );
-    let pos = InsertPosition::Before(lhs_tl.r_curly_token()?.into());
-    let use_tree_list = lhs_tl.insert_children(pos, to_insert);
-    Some(lhs.with_use_tree_list(use_tree_list))
+    let count = use_trees.len();
+    let tl = make::use_tree_list(use_trees);
+    Some((lhs.with_use_tree_list(tl), count))
 }
 
 /// Traverses both paths until they differ, returning the common prefix of both.
@@ -235,6 +322,23 @@ fn common_prefix(lhs: &ast::Path, rhs: &ast::Path) -> Option<(ast::Path, ast::Pa
     res
 }
 
+fn path_is_self(path: ast::Path) -> bool {
+    path.segment().and_then(|seg| seg.self_token()).is_some() && path.qualifier().is_none()
+}
+
+fn first_segment(path: &ast::Path) -> Option<ast::PathSegment> {
+    first_path(path).segment()
+}
+
+fn first_path(path: &ast::Path) -> ast::Path {
+    successors(Some(path.clone()), ast::Path::qualifier).last().unwrap()
+}
+
+fn segment_iter(path: &ast::Path) -> impl Iterator<Item = ast::PathSegment> + Clone {
+    // cant make use of SyntaxNode::siblings, because the returned Iterator is not clone
+    successors(first_segment(path), |p| p.parent_path().parent_path().and_then(|p| p.segment()))
+}
+
 /// What type of merges are allowed.
 #[derive(Copy, Clone, PartialEq, Eq)]
 pub enum MergeBehaviour {
@@ -279,19 +383,6 @@ impl ImportGroup {
     }
 }
 
-fn first_segment(path: &ast::Path) -> Option<ast::PathSegment> {
-    first_path(path).segment()
-}
-
-fn first_path(path: &ast::Path) -> ast::Path {
-    successors(Some(path.clone()), ast::Path::qualifier).last().unwrap()
-}
-
-fn segment_iter(path: &ast::Path) -> impl Iterator<Item = ast::PathSegment> + Clone {
-    // cant make use of SyntaxNode::siblings, because the returned Iterator is not clone
-    successors(first_segment(path), |p| p.parent_path().parent_path().and_then(|p| p.segment()))
-}
-
 #[derive(PartialEq, Eq)]
 enum AddBlankLine {
     Before,
@@ -594,7 +685,7 @@ use std::io;",
         check_full(
             "std::foo::bar::Baz",
             r"use std::foo::bar::Qux;",
-            r"use std::foo::bar::{Qux, Baz};",
+            r"use std::foo::bar::{Baz, Qux};",
         )
     }
 
@@ -603,7 +694,7 @@ use std::io;",
         check_last(
             "std::foo::bar::Baz",
             r"use std::foo::bar::Qux;",
-            r"use std::foo::bar::{Qux, Baz};",
+            r"use std::foo::bar::{Baz, Qux};",
         )
     }
 
@@ -612,7 +703,7 @@ use std::io;",
         check_full(
             "std::foo::bar::Baz",
             r"use std::foo::bar::{Qux, Quux};",
-            r"use std::foo::bar::{Qux, Quux, Baz};",
+            r"use std::foo::bar::{Baz, Quux, Qux};",
         )
     }
 
@@ -621,7 +712,7 @@ use std::io;",
         check_last(
             "std::foo::bar::Baz",
             r"use std::foo::bar::{Qux, Quux};",
-            r"use std::foo::bar::{Qux, Quux, Baz};",
+            r"use std::foo::bar::{Baz, Quux, Qux};",
         )
     }
 
@@ -630,7 +721,7 @@ use std::io;",
         check_full(
             "std::foo::bar::Baz",
             r"use std::foo::bar::{Qux, quux::{Fez, Fizz}};",
-            r"use std::foo::bar::{Qux, quux::{Fez, Fizz}, Baz};",
+            r"use std::foo::bar::{Baz, Qux, quux::{Fez, Fizz}};",
         )
     }
 
@@ -644,6 +735,15 @@ use std::foo::bar::{Qux, quux::{Fez, Fizz}};",
         )
     }
 
+    #[test]
+    fn merge_groups_full_nested_deep() {
+        check_full(
+            "std::foo::bar::quux::Baz",
+            r"use std::foo::bar::{Qux, quux::{Fez, Fizz}};",
+            r"use std::foo::bar::{Qux, quux::{Baz, Fez, Fizz}};",
+        )
+    }
+
     #[test]
     fn merge_groups_skip_pub() {
         check_full(
@@ -670,34 +770,63 @@ use std::io;",
         check_last(
             "std::fmt::Result",
             r"use std::{fmt, io};",
-            r"use std::{self, fmt::Result};
+            r"use std::fmt::{self, Result};
 use std::io;",
         )
     }
 
+    #[test]
+    fn merge_into_module_import() {
+        check_full(
+            "std::fmt::Result",
+            r"use std::{fmt, io};",
+            r"use std::{fmt::{self, Result}, io};",
+        )
+    }
+
     #[test]
     fn merge_groups_self() {
         check_full("std::fmt::Debug", r"use std::fmt;", r"use std::fmt::{self, Debug};")
     }
 
     #[test]
-    fn merge_self_glob() {
+    fn merge_mod_into_glob() {
         check_full(
             "token::TokenKind",
             r"use token::TokenKind::*;",
             r"use token::TokenKind::{self::*, self};",
         )
+        // FIXME: have it emit `use token::TokenKind::{self, *}`?
+    }
+
+    #[test]
+    fn merge_self_glob() {
+        check_full("self", r"use self::*;", r"use self::{self::*, self};")
+        // FIXME: have it emit `use {self, *}`?
+    }
+
+    #[test]
+    #[ignore] // FIXME: Support this
+    fn merge_partial_path() {
+        check_full(
+            "ast::Foo",
+            r"use syntax::{ast, algo};",
+            r"use syntax::{ast::{self, Foo}, algo};",
+        )
+    }
+
+    #[test]
+    fn merge_glob_nested() {
+        check_full(
+            "foo::bar::quux::Fez",
+            r"use foo::bar::{Baz, quux::*;",
+            r"use foo::bar::{Baz, quux::{self::*, Fez}}",
+        )
     }
 
     #[test]
     fn merge_last_too_long() {
-        mark::check!(test_last_merge_too_long);
-        check_last(
-            "foo::bar",
-            r"use foo::bar::baz::Qux;",
-            r"use foo::bar;
-use foo::bar::baz::Qux;",
-        );
+        check_last("foo::bar", r"use foo::bar::baz::Qux;", r"use foo::bar::{self, baz::Qux};");
     }
 
     #[test]
@@ -710,6 +839,42 @@ use foo::bar::baz::Qux;",
         );
     }
 
+    #[test]
+    fn merge_last_fail() {
+        check_merge_only_fail(
+            r"use foo::bar::{baz::{Qux, Fez}};",
+            r"use foo::bar::{baaz::{Quux, Feez}};",
+            MergeBehaviour::Last,
+        );
+    }
+
+    #[test]
+    fn merge_last_fail1() {
+        check_merge_only_fail(
+            r"use foo::bar::{baz::{Qux, Fez}};",
+            r"use foo::bar::baaz::{Quux, Feez};",
+            MergeBehaviour::Last,
+        );
+    }
+
+    #[test]
+    fn merge_last_fail2() {
+        check_merge_only_fail(
+            r"use foo::bar::baz::{Qux, Fez};",
+            r"use foo::bar::{baaz::{Quux, Feez}};",
+            MergeBehaviour::Last,
+        );
+    }
+
+    #[test]
+    fn merge_last_fail3() {
+        check_merge_only_fail(
+            r"use foo::bar::baz::{Qux, Fez};",
+            r"use foo::bar::baaz::{Quux, Feez};",
+            MergeBehaviour::Last,
+        );
+    }
+
     fn check(
         path: &str,
         ra_fixture_before: &str,
@@ -742,4 +907,23 @@ use foo::bar::baz::Qux;",
     fn check_none(path: &str, ra_fixture_before: &str, ra_fixture_after: &str) {
         check(path, ra_fixture_before, ra_fixture_after, None)
     }
+
+    fn check_merge_only_fail(ra_fixture0: &str, ra_fixture1: &str, mb: MergeBehaviour) {
+        let use0 = ast::SourceFile::parse(ra_fixture0)
+            .tree()
+            .syntax()
+            .descendants()
+            .find_map(ast::Use::cast)
+            .unwrap();
+
+        let use1 = ast::SourceFile::parse(ra_fixture1)
+            .tree()
+            .syntax()
+            .descendants()
+            .find_map(ast::Use::cast)
+            .unwrap();
+
+        let result = try_merge_imports(&use0, &use1, mb);
+        assert_eq!(result, None);
+    }
 }
diff --git a/crates/syntax/src/ast/edit.rs b/crates/syntax/src/ast/edit.rs
index 8b1c65dd6f..45cf31f130 100644
--- a/crates/syntax/src/ast/edit.rs
+++ b/crates/syntax/src/ast/edit.rs
@@ -347,6 +347,7 @@ impl ast::UseTree {
         self.clone()
     }
 
+    /// Splits off the given prefix, making it the path component of the use tree, appending the rest of the path to all UseTreeList items.
     #[must_use]
     pub fn split_prefix(&self, prefix: &ast::Path) -> ast::UseTree {
         let suffix = if self.path().as_ref() == Some(prefix) && self.use_tree_list().is_none() {