diff --git a/backend/reconcile/src/diffs/raw_operation.rs b/backend/reconcile/src/diffs/raw_operation.rs
index 0df48f5..f95a034 100644
--- a/backend/reconcile/src/diffs/raw_operation.rs
+++ b/backend/reconcile/src/diffs/raw_operation.rs
@@ -28,10 +28,26 @@ where
 
     pub fn get_original_text(self) -> String { self.tokens().iter().map(Token::original).collect() }
 
-    /// Extends the operation with another operation if returning the new
-    /// operation. Only operations of the same type can be used to extend.
-    /// If the operations are of different types, returns None.
+    pub fn is_left_joinable(&self) -> bool {
+        let first_token = self.tokens().first();
+        first_token.map_or(true, |t| t.get_is_left_joinable())
+    }
+
+    pub fn is_right_joinable(&self) -> bool {
+        let last_token = self.tokens().last();
+        last_token.map_or(true, |t| t.get_is_right_joinable())
+    }
+
+    /// Extends the operation with another operation when it returns Some
+    /// operation. Only operations of the same type as self can be used to
+    /// extend self. If the operations are of different types, returns None.
     pub fn extend(self, other: RawOperation<T>) -> Option<RawOperation<T>> {
+        debug_assert!(
+            std::mem::discriminant(&self) == std::mem::discriminant(&other),
+            "Cannot extend operations of different types. This should have been handled before \
+             calling this function."
+        );
+
         match (self, other) {
             (RawOperation::Insert(tokens1), RawOperation::Insert(tokens2)) => Some(
                 RawOperation::Insert(tokens1.into_iter().chain(tokens2).collect()),
@@ -42,7 +58,7 @@ where
             (RawOperation::Equal(tokens1), RawOperation::Equal(tokens2)) => Some(
                 RawOperation::Equal(tokens1.into_iter().chain(tokens2).collect()),
             ),
-            _ => None,
+            _ => unreachable!("Only operations of the same type can be extended"),
         }
     }
 }
diff --git a/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__complex_diff.snap b/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__complex_diff.snap
index 8c89ed3..57ee086 100644
--- a/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__complex_diff.snap
+++ b/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__complex_diff.snap
@@ -9,6 +9,8 @@ snapshot_kind: text
             Token {
                 normalised: "a",
                 original: "a",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
         ],
     ),
@@ -17,6 +19,8 @@ snapshot_kind: text
             Token {
                 normalised: "x",
                 original: "x",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
         ],
     ),
@@ -25,6 +29,8 @@ snapshot_kind: text
             Token {
                 normalised: "b",
                 original: "b",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
         ],
     ),
@@ -33,6 +39,8 @@ snapshot_kind: text
             Token {
                 normalised: "c",
                 original: "c",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
         ],
     ),
@@ -41,6 +49,8 @@ snapshot_kind: text
             Token {
                 normalised: "y",
                 original: "y",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
         ],
     ),
@@ -49,6 +59,8 @@ snapshot_kind: text
             Token {
                 normalised: "d",
                 original: "d",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
         ],
     ),
diff --git a/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__delete_only.snap b/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__delete_only.snap
index f07eb3d..a4598d0 100644
--- a/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__delete_only.snap
+++ b/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__delete_only.snap
@@ -9,10 +9,14 @@ snapshot_kind: text
             Token {
                 normalised: "a",
                 original: "a",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
             Token {
                 normalised: "b",
                 original: "b",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
         ],
     ),
diff --git a/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__identical_content.snap b/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__identical_content.snap
index a99e276..2fc3317 100644
--- a/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__identical_content.snap
+++ b/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__identical_content.snap
@@ -9,14 +9,20 @@ snapshot_kind: text
             Token {
                 normalised: "a",
                 original: "a",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
             Token {
                 normalised: "b",
                 original: "b",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
             Token {
                 normalised: "c",
                 original: "c",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
         ],
     ),
diff --git a/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__insert_only.snap b/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__insert_only.snap
index b32c8ce..e07d844 100644
--- a/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__insert_only.snap
+++ b/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__insert_only.snap
@@ -9,10 +9,14 @@ snapshot_kind: text
             Token {
                 normalised: "a",
                 original: "a",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
             Token {
                 normalised: "b",
                 original: "b",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
         ],
     ),
diff --git a/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__prefix_and_suffix.snap b/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__prefix_and_suffix.snap
index 03c8fee..6b86600 100644
--- a/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__prefix_and_suffix.snap
+++ b/backend/reconcile/src/diffs/snapshots/reconcile__diffs__myers__tests__prefix_and_suffix.snap
@@ -9,6 +9,8 @@ snapshot_kind: text
             Token {
                 normalised: "a",
                 original: "a",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
         ],
     ),
@@ -17,10 +19,14 @@ snapshot_kind: text
             Token {
                 normalised: "b",
                 original: "b",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
             Token {
                 normalised: "c",
                 original: "c",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
         ],
     ),
@@ -29,6 +35,8 @@ snapshot_kind: text
             Token {
                 normalised: "x",
                 original: "x",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
         ],
     ),
@@ -37,6 +45,8 @@ snapshot_kind: text
             Token {
                 normalised: "d",
                 original: "d",
+                is_left_joinable: true,
+                is_right_joinable: true,
             },
         ],
     ),
diff --git a/backend/reconcile/src/operation_transformation/edited_text.rs b/backend/reconcile/src/operation_transformation/edited_text.rs
index 8fc2ed9..fdaa87f 100644
--- a/backend/reconcile/src/operation_transformation/edited_text.rs
+++ b/backend/reconcile/src/operation_transformation/edited_text.rs
@@ -3,15 +3,12 @@ use core::iter;
 #[cfg(feature = "serde")]
 use serde::{Deserialize, Serialize};
 
-use super::{CursorPosition, Operation, TextWithCursors};
+use super::{CursorPosition, Operation, TextWithCursors, ordered_operation::OrderedOperation};
 use crate::{
     diffs::{myers::diff, raw_operation::RawOperation},
     operation_transformation::merge_context::MergeContext,
     tokenizer::{Tokenizer, word_tokenizer::word_tokenizer},
-    utils::{
-        merge_iters::MergeSorted as _, ordered_operation::OrderedOperation, side::Side,
-        string_builder::StringBuilder,
-    },
+    utils::{merge_iters::MergeSorted as _, side::Side, string_builder::StringBuilder},
 };
 
 /// A sequence of operations that can be applied to a text document.
@@ -66,11 +63,93 @@ where
 
         Self::new(
             original,
-            Self::cook_operations(Self::elongate_operations(diff)).collect(),
+            Self::cook_operations(Self::elongate_operations(Self::break_up_raw_operations(
+                diff,
+            )))
+            .collect(),
             updated.cursors,
         )
     }
 
+    fn break_up_raw_operations<I>(raw_operations: I) -> impl Iterator<Item = RawOperation<T>>
+    where
+        I: IntoIterator<Item = RawOperation<T>>,
+    {
+        raw_operations.into_iter().flat_map(|raw_operation| {
+            let mut result: Vec<RawOperation<T>> = Vec::new();
+            match raw_operation {
+                RawOperation::Insert(tokens) => {
+                    for token in tokens {
+                        result.push(RawOperation::Insert(vec![token]));
+                    }
+                }
+                RawOperation::Delete(tokens) => {
+                    for token in tokens {
+                        result.push(RawOperation::Delete(vec![token]));
+                    }
+                }
+                RawOperation::Equal(tokens) => {
+                    for token in tokens {
+                        result.push(RawOperation::Equal(vec![token]));
+                    }
+                }
+            }
+            result.into_iter()
+        })
+    }
+
+    fn elongate_operations<I>(raw_operations: I) -> Vec<RawOperation<T>>
+    where
+        I: IntoIterator<Item = RawOperation<T>>,
+    {
+        let mut maybe_previous_insert: Option<RawOperation<T>> = None;
+        let mut maybe_previous_delete: Option<RawOperation<T>> = None;
+
+        let mut result: Vec<RawOperation<T>> = raw_operations
+            .into_iter()
+            .flat_map(|next| match next {
+                RawOperation::Insert(..) => match maybe_previous_insert.take() {
+                    Some(prev) if prev.is_right_joinable() && next.is_left_joinable() => {
+                        maybe_previous_insert = prev.extend(next);
+                        Box::new(iter::empty()) as Box<dyn Iterator<Item = RawOperation<T>>>
+                    }
+                    prev => {
+                        maybe_previous_insert = Some(next);
+                        Box::new(prev.into_iter())
+                    }
+                },
+                RawOperation::Delete(..) => match maybe_previous_delete.take() {
+                    Some(prev) if prev.is_right_joinable() && next.is_left_joinable() => {
+                        maybe_previous_delete = prev.extend(next);
+                        Box::new(iter::empty()) as Box<dyn Iterator<Item = RawOperation<T>>>
+                    }
+                    prev => {
+                        maybe_previous_delete = Some(next);
+                        Box::new(prev.into_iter())
+                    }
+                },
+                RawOperation::Equal(..) => Box::new(
+                    maybe_previous_insert
+                        .take()
+                        .into_iter()
+                        .chain(maybe_previous_delete.take())
+                        .chain(iter::once(next)),
+                )
+                    as Box<dyn Iterator<Item = RawOperation<T>>>,
+            })
+            .collect();
+
+        if let Some(prev) = maybe_previous_insert {
+            result.push(prev);
+        }
+
+        if let Some(prev) = maybe_previous_delete {
+            result.push(prev);
+        }
+
+        result
+    }
+
     // Turn raw operations into ordered operations while keeping track of old & new
     // indexes.
     fn cook_operations<I>(raw_operations: I) -> impl Iterator<Item = OrderedOperation<T>>
@@ -119,56 +198,6 @@ where
         })
     }
 
-    fn elongate_operations<I>(raw_operations: I) -> Vec<RawOperation<T>>
-    where
-        I: IntoIterator<Item = RawOperation<T>>,
-    {
-        let mut maybe_previous_insert: Option<RawOperation<T>> = None;
-        let mut maybe_previous_delete: Option<RawOperation<T>> = None;
-
-        let mut result: Vec<RawOperation<T>> = raw_operations
-            .into_iter()
-            .flat_map(|next| match next {
-                RawOperation::Insert(..) => {
-                    if let Some(prev) = maybe_previous_insert.take() {
-                        maybe_previous_insert = prev.extend(next);
-                    } else {
-                        maybe_previous_insert = Some(next);
-                    }
-
-                    Box::new(iter::empty()) as Box<dyn Iterator<Item = RawOperation<T>>>
-                }
-                RawOperation::Delete(..) => {
-                    if let Some(prev) = maybe_previous_delete.take() {
-                        maybe_previous_delete = prev.extend(next);
-                    } else {
-                        maybe_previous_delete = Some(next);
-                    }
-
-                    Box::new(iter::empty()) as Box<dyn Iterator<Item = RawOperation<T>>>
-                }
-                RawOperation::Equal(..) => Box::new(
-                    maybe_previous_insert
-                        .take()
-                        .into_iter()
-                        .chain(maybe_previous_delete.take())
-                        .chain(iter::once(next)),
-                )
-                    as Box<dyn Iterator<Item = RawOperation<T>>>,
-            })
-            .collect();
-
-        if let Some(prev) = maybe_previous_insert {
-            result.push(prev);
-        }
-
-        if let Some(prev) = maybe_previous_delete {
-            result.push(prev);
-        }
-
-        result
-    }
-
     /// Create a new `EditedText` with the given operations.
     /// The operations must be in the order in which they are meant to be
     /// applied. The operations must not overlap.
@@ -225,6 +254,7 @@ where
                         // Operations on the left and right must come in the same order so that
                         // inserts can be merged with other inserts and deletes with deletes.
                         usize::from(matches!(operation.operation, Operation::Delete { .. })),
+                        operation.operation.start_index(),
                         // Make sure that the ordering is deterministic regardless which text
                         // is left or right.
                         match &operation.operation {
diff --git a/backend/reconcile/src/tokenizer/snapshots/reconcile__tokenizer__word_tokenizer__tests__with_snapshots-3.snap b/backend/reconcile/src/tokenizer/snapshots/reconcile__tokenizer__word_tokenizer__tests__with_snapshots-3.snap
index 58d749e..d1c94e1 100644
--- a/backend/reconcile/src/tokenizer/snapshots/reconcile__tokenizer__word_tokenizer__tests__with_snapshots-3.snap
+++ b/backend/reconcile/src/tokenizer/snapshots/reconcile__tokenizer__word_tokenizer__tests__with_snapshots-3.snap
@@ -5,11 +5,21 @@ snapshot_kind: text
 ---
 [
     Token {
-        normalised: "what?",
-        original: " what?",
+        normalised: " what?",
+        original: " ",
+        is_left_joinable: true,
+        is_right_joinable: true,
     },
     Token {
-        normalised: "",
+        normalised: "what?",
+        original: "what?",
+        is_left_joinable: true,
+        is_right_joinable: true,
+    },
+    Token {
+        normalised: " ",
         original: " ",
+        is_left_joinable: true,
+        is_right_joinable: true,
     },
 ]
diff --git a/backend/reconcile/src/tokenizer/snapshots/reconcile__tokenizer__word_tokenizer__tests__with_snapshots-4.snap b/backend/reconcile/src/tokenizer/snapshots/reconcile__tokenizer__word_tokenizer__tests__with_snapshots-4.snap
index 4c28a7f..6740dbc 100644
--- a/backend/reconcile/src/tokenizer/snapshots/reconcile__tokenizer__word_tokenizer__tests__with_snapshots-4.snap
+++ b/backend/reconcile/src/tokenizer/snapshots/reconcile__tokenizer__word_tokenizer__tests__with_snapshots-4.snap
@@ -4,20 +4,52 @@ expression: "word_tokenizer(\" hello, \\nwhere are you?\")"
 snapshot_kind: text
 ---
 [
+    Token {
+        normalised: " hello,",
+        original: " ",
+        is_left_joinable: true,
+        is_right_joinable: true,
+    },
     Token {
         normalised: "hello,",
-        original: " hello,",
+        original: "hello,",
+        is_left_joinable: true,
+        is_right_joinable: true,
+    },
+    Token {
+        normalised: " \nwhere",
+        original: " \n",
+        is_left_joinable: true,
+        is_right_joinable: true,
     },
     Token {
         normalised: "where",
-        original: " \nwhere",
+        original: "where",
+        is_left_joinable: true,
+        is_right_joinable: true,
+    },
+    Token {
+        normalised: " are",
+        original: " ",
+        is_left_joinable: true,
+        is_right_joinable: true,
     },
     Token {
         normalised: "are",
-        original: " are",
+        original: "are",
+        is_left_joinable: true,
+        is_right_joinable: true,
+    },
+    Token {
+        normalised: " you?",
+        original: " ",
+        is_left_joinable: true,
+        is_right_joinable: true,
     },
     Token {
         normalised: "you?",
-        original: " you?",
+        original: "you?",
+        is_left_joinable: true,
+        is_right_joinable: true,
     },
 ]
diff --git a/backend/reconcile/src/tokenizer/snapshots/reconcile__tokenizer__word_tokenizer__tests__with_snapshots-5.snap b/backend/reconcile/src/tokenizer/snapshots/reconcile__tokenizer__word_tokenizer__tests__with_snapshots-5.snap
new file mode 100644
index 0000000..832147e
--- /dev/null
+++ b/backend/reconcile/src/tokenizer/snapshots/reconcile__tokenizer__word_tokenizer__tests__with_snapshots-5.snap
@@ -0,0 +1,39 @@
+---
+source: reconcile/src/tokenizer/word_tokenizer.rs
+expression: "word_tokenizer(\" hello, \\nwhere are you?\")"
+snapshot_kind: text
+---
+[
+    Token {
+        normalised: " ",
+        original: " ",
+    },
+    Token {
+        normalised: "hello,",
+        original: "hello,",
+    },
+    Token {
+        normalised: " \n",
+        original: " \n",
+    },
+    Token {
+        normalised: "where",
+        original: "where",
+    },
+    Token {
+        normalised: " ",
+        original: " ",
+    },
+    Token {
+        normalised: "are",
+        original: "are",
+    },
+    Token {
+        normalised: " ",
+        original: " ",
+    },
+    Token {
+        normalised: "you?",
+        original: "you?",
+    },
+]
diff --git a/backend/reconcile/src/tokenizer/snapshots/reconcile__tokenizer__word_tokenizer__tests__with_snapshots.snap b/backend/reconcile/src/tokenizer/snapshots/reconcile__tokenizer__word_tokenizer__tests__with_snapshots.snap
index 206c7fe..95c8db5 100644
--- a/backend/reconcile/src/tokenizer/snapshots/reconcile__tokenizer__word_tokenizer__tests__with_snapshots.snap
+++ b/backend/reconcile/src/tokenizer/snapshots/reconcile__tokenizer__word_tokenizer__tests__with_snapshots.snap
@@ -7,9 +7,19 @@ snapshot_kind: text
     Token {
         normalised: "Hi",
         original: "Hi",
+        is_left_joinable: true,
+        is_right_joinable: true,
+    },
+    Token {
+        normalised: " there!",
+        original: " ",
+        is_left_joinable: true,
+        is_right_joinable: true,
     },
     Token {
         normalised: "there!",
-        original: " there!",
+        original: "there!",
+        is_left_joinable: true,
+        is_right_joinable: true,
     },
 ]
diff --git a/backend/reconcile/src/tokenizer/token.rs b/backend/reconcile/src/tokenizer/token.rs
index ab521a7..86cbb92 100644
--- a/backend/reconcile/src/tokenizer/token.rs
+++ b/backend/reconcile/src/tokenizer/token.rs
@@ -3,29 +3,45 @@ use serde::{Deserialize, Serialize};
 
 /// A token is a string that has been normalised in some way.
 /// The normalised form is used for comparison, while the original form is used
-/// for applying Operations.
+/// for applying `Operation`-s.
 #[cfg_attr(feature = "serde", derive(Serialize, Deserialize))]
 #[derive(Debug, Clone)]
 pub struct Token<T>
 where
     T: PartialEq + Clone + std::fmt::Debug,
 {
-    normalised: T,
+    /// The normalised form of the token used deriving the diff.
+    pub normalised: T,
+
+    /// The original string, that should be inserted or deleted in the document.
     original: String,
+
+    /// Whether the token is joinable with the previous token.
+    is_left_joinable: bool,
+
+    /// Whether the token is joinable with the next token.
+    is_right_joinable: bool,
 }
 
 impl From<&str> for Token<String> {
-    fn from(s: &str) -> Self { Token::new(s.trim().to_owned(), s.to_owned()) }
+    fn from(text: &str) -> Self { Token::new(text.to_owned(), text.to_owned(), true, true) }
 }
 
 impl<T> Token<T>
 where
     T: PartialEq + Clone + std::fmt::Debug,
 {
-    pub fn new(normalised: T, original: String) -> Self {
+    pub fn new(
+        normalised: T,
+        original: String,
+        is_left_joinable: bool,
+        is_right_joinable: bool,
+    ) -> Self {
         Token {
             normalised,
             original,
+            is_left_joinable,
+            is_right_joinable,
         }
     }
 
@@ -34,6 +50,10 @@ where
     pub fn normalised(&self) -> &T { &self.normalised }
 
     pub fn get_original_length(&self) -> usize { self.original.chars().count() }
+
+    pub fn get_is_left_joinable(&self) -> bool { self.is_left_joinable }
+
+    pub fn get_is_right_joinable(&self) -> bool { self.is_right_joinable }
 }
 
 impl<T> PartialEq for Token<T>
diff --git a/backend/reconcile/tests/examples/multiline.yml b/backend/reconcile/tests/examples/multiline.yml
index c751feb..00de7cd 100644
--- a/backend/reconcile/tests/examples/multiline.yml
+++ b/backend/reconcile/tests/examples/multiline.yml
@@ -7,14 +7,59 @@ left: |
 right: |
   Hello there!
 
-
   Best,
   Andras
 
 expected: |
   Hello there!
 
-  How are you?
-
   Best,
   Andras
+
+
+  How are you?
+
+---
+
+parent: |
+  - my list
+  - 2nd item
+  - 3rd item
+
+left: |
+  - my list
+  - 2nd item
+      - nested list
+        - very nested  list
+  - 3rd item
+
+right: |
+  - my list
+    - nested list
+  - 2nd item
+  - 3rd item
+    - another nested list
+
+expected: |
+  - my list
+    - nested list
+  - 2nd item
+      - nested list
+        - very nested  list
+  - 3rd item
+    - another nested list
+
+---
+
+parent: |
+  a
+  a
+left: |
+  a
+    a
+right: |
+  a
+  a
+expected: |
+  a
+    a