diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_simplify/SIM905.py b/crates/ruff_linter/resources/test/fixtures/flake8_simplify/SIM905.py
index 1545b07ca8..a8dc8fe996 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_simplify/SIM905.py
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_simplify/SIM905.py
@@ -171,3 +171,10 @@ print("<\x1c\x1d\x1e\x1f".rsplit(maxsplit=0))
 " a b c d ".split(maxsplit=2)  # ["a", "b", "c d "]
 " a b c d ".rsplit(maxsplit=2)  # [" a b", "c", "d"]
 "a  b".split(maxsplit=1)  # ["a", "b"]
+
+# https://github.com/astral-sh/ruff/issues/19610
+r"1" "\n".split("1")  # [r"", "\n"]
+r"" "\"".split("1")  # ['"']
+r"1" """
+""".split("1")  # [r"", "\n"]
+r"\n" "\n'\"".split("1")  # ["\\n\n'\""]
diff --git a/crates/ruff_linter/src/rules/flake8_simplify/rules/split_static_string.rs b/crates/ruff_linter/src/rules/flake8_simplify/rules/split_static_string.rs
index ffd4ee30c5..a38886772e 100644
--- a/crates/ruff_linter/src/rules/flake8_simplify/rules/split_static_string.rs
+++ b/crates/ruff_linter/src/rules/flake8_simplify/rules/split_static_string.rs
@@ -1,8 +1,7 @@
 use ruff_macros::{ViolationMetadata, derive_message_formats};
-use ruff_python_ast::StringFlags;
 use ruff_python_ast::{
-    Expr, ExprCall, ExprContext, ExprList, ExprUnaryOp, StringLiteral, StringLiteralFlags,
-    StringLiteralValue, UnaryOp, str::TripleQuotes,
+    Expr, ExprCall, ExprContext, ExprList, ExprUnaryOp, StringFlags, StringLiteral,
+    StringLiteralFlags, StringLiteralValue, UnaryOp,
 };
 use ruff_text_size::{Ranged, TextRange};
 use std::cmp::Ordering;
@@ -158,21 +157,26 @@ fn replace_flags(elt: &str, flags: StringLiteralFlags) -> StringLiteralFlags {
     // 'single'quoted
     // """.split() # -> [r"itemA",r"'single'quoted'"]
     // ```
-    if !flags.prefix().is_raw() || !elt.contains(flags.quote_style().as_char()) {
-        flags.with_triple_quotes(TripleQuotes::No)
-    }
-    // If we have a raw string containing a quotation mark of the same style,
-    // then we have to swap the style of quotation marks used
-    else if !elt.contains(flags.quote_style().opposite().as_char()) {
-        flags
-            .with_quote_style(flags.quote_style().opposite())
-            .with_triple_quotes(TripleQuotes::No)
-    } else
-    // If both types of quotes are used in the raw, triple-quoted string, then
-    // we are forced to either add escapes or keep the triple quotes. We opt for
-    // the latter.
-    {
-        flags
+    if !flags.prefix().is_raw() {
+        flags.with_triple_quotes(ruff_python_ast::str::TripleQuotes::No)
+    } else if elt.contains(['\n', '\r']) {
+        // If the element contains newlines or carriage returns, we need to use
+        // default flags (no raw prefix) to avoid syntax errors
+        StringLiteralFlags::empty()
+    } else if elt.contains(flags.quote_style().as_char()) {
+        // If we have a raw string containing a quotation mark of the same style,
+        // then we have to swap the style of quotation marks used
+        if elt.contains(flags.quote_style().opposite().as_char()) {
+            // If both types of quotes are used in the raw string, then
+            // we are forced to use default flags to avoid syntax errors
+            StringLiteralFlags::empty()
+        } else {
+            flags
+                .with_quote_style(flags.quote_style().opposite())
+                .with_triple_quotes(ruff_python_ast::str::TripleQuotes::No)
+        }
+    } else {
+        flags.with_triple_quotes(ruff_python_ast::str::TripleQuotes::No)
     }
 }
 
diff --git a/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__SIM905_SIM905.py.snap b/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__SIM905_SIM905.py.snap
index 2cadf0ceb9..961048deeb 100644
--- a/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__SIM905_SIM905.py.snap
+++ b/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__SIM905_SIM905.py.snap
@@ -1302,7 +1302,7 @@ help: Replace with list literal
     - 'no need' to escape
     - "swap" quote style
     - "use' ugly triple quotes""".split("\n")
-160 + [r"first", r"'no need' to escape", r'"swap" quote style', r""""use' ugly triple quotes"""]
+160 + [r"first", r"'no need' to escape", r'"swap" quote style', '"use\' ugly triple quotes']
 161 | 
 162 | # https://github.com/astral-sh/ruff/issues/19845
 163 | print("S\x1cP\x1dL\x1eI\x1fT".split())
@@ -1394,5 +1394,80 @@ SIM905 Consider using a list literal instead of `str.split`
 172 | " a b c d ".rsplit(maxsplit=2)  # [" a b", "c", "d"]
 173 | "a  b".split(maxsplit=1)  # ["a", "b"]
     | ^^^^^^^^^^^^^^^^^^^^^^^^
+174 |
+175 | # https://github.com/astral-sh/ruff/issues/19610
     |
 help: Replace with list literal
+
+SIM905 [*] Consider using a list literal instead of `str.split`
+   --> SIM905.py:176:1
+    |
+175 | # https://github.com/astral-sh/ruff/issues/19610
+176 | r"1" "\n".split("1")  # [r"", "\n"]
+    | ^^^^^^^^^^^^^^^^^^^^
+177 | r"" "\"".split("1")  # ['"']
+178 | r"1" """
+    |
+help: Replace with list literal
+173 | "a  b".split(maxsplit=1)  # ["a", "b"]
+174 | 
+175 | # https://github.com/astral-sh/ruff/issues/19610
+    - r"1" "\n".split("1")  # [r"", "\n"]
+176 + [r"", '\n']  # [r"", "\n"]
+177 | r"" "\"".split("1")  # ['"']
+178 | r"1" """
+179 | """.split("1")  # [r"", "\n"]
+
+SIM905 [*] Consider using a list literal instead of `str.split`
+   --> SIM905.py:177:1
+    |
+175 | # https://github.com/astral-sh/ruff/issues/19610
+176 | r"1" "\n".split("1")  # [r"", "\n"]
+177 | r"" "\"".split("1")  # ['"']
+    | ^^^^^^^^^^^^^^^^^^^
+178 | r"1" """
+179 | """.split("1")  # [r"", "\n"]
+    |
+help: Replace with list literal
+174 | 
+175 | # https://github.com/astral-sh/ruff/issues/19610
+176 | r"1" "\n".split("1")  # [r"", "\n"]
+    - r"" "\"".split("1")  # ['"']
+177 + [r'"']  # ['"']
+178 | r"1" """
+179 | """.split("1")  # [r"", "\n"]
+180 | r"\n" "\n'\"".split("1")  # ["\\n\n'\""]
+
+SIM905 [*] Consider using a list literal instead of `str.split`
+   --> SIM905.py:178:1
+    |
+176 |   r"1" "\n".split("1")  # [r"", "\n"]
+177 |   r"" "\"".split("1")  # ['"']
+178 | / r"1" """
+179 | | """.split("1")  # [r"", "\n"]
+    | |______________^
+180 |   r"\n" "\n'\"".split("1")  # ["\\n\n'\""]
+    |
+help: Replace with list literal
+175 | # https://github.com/astral-sh/ruff/issues/19610
+176 | r"1" "\n".split("1")  # [r"", "\n"]
+177 | r"" "\"".split("1")  # ['"']
+    - r"1" """
+    - """.split("1")  # [r"", "\n"]
+178 + [r"", '\n']  # [r"", "\n"]
+179 | r"\n" "\n'\"".split("1")  # ["\\n\n'\""]
+
+SIM905 [*] Consider using a list literal instead of `str.split`
+   --> SIM905.py:180:1
+    |
+178 | r"1" """
+179 | """.split("1")  # [r"", "\n"]
+180 | r"\n" "\n'\"".split("1")  # ["\\n\n'\""]
+    | ^^^^^^^^^^^^^^^^^^^^^^^^
+    |
+help: Replace with list literal
+177 | r"" "\"".split("1")  # ['"']
+178 | r"1" """
+179 | """.split("1")  # [r"", "\n"]
+    - r"\n" "\n'\"".split("1")  # ["\\n\n'\""]
+180 + ['\\n\n\'"']  # ["\\n\n'\""]
diff --git a/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__preview__SIM905_SIM905.py.snap b/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__preview__SIM905_SIM905.py.snap
index d477367205..d224c4581f 100644
--- a/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__preview__SIM905_SIM905.py.snap
+++ b/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__preview__SIM905_SIM905.py.snap
@@ -1350,7 +1350,7 @@ help: Replace with list literal
     - 'no need' to escape
     - "swap" quote style
     - "use' ugly triple quotes""".split("\n")
-160 + [r"first", r"'no need' to escape", r'"swap" quote style', r""""use' ugly triple quotes"""]
+160 + [r"first", r"'no need' to escape", r'"swap" quote style', '"use\' ugly triple quotes']
 161 | 
 162 | # https://github.com/astral-sh/ruff/issues/19845
 163 | print("S\x1cP\x1dL\x1eI\x1fT".split())
@@ -1430,6 +1430,7 @@ help: Replace with list literal
 171 + ["a", "b", "c d "]  # ["a", "b", "c d "]
 172 | " a b c d ".rsplit(maxsplit=2)  # [" a b", "c", "d"]
 173 | "a  b".split(maxsplit=1)  # ["a", "b"]
+174 | 
 
 SIM905 [*] Consider using a list literal instead of `str.rsplit`
    --> SIM905.py:172:1
@@ -1447,6 +1448,8 @@ help: Replace with list literal
     - " a b c d ".rsplit(maxsplit=2)  # [" a b", "c", "d"]
 172 + [" a b", "c", "d"]  # [" a b", "c", "d"]
 173 | "a  b".split(maxsplit=1)  # ["a", "b"]
+174 | 
+175 | # https://github.com/astral-sh/ruff/issues/19610
 
 SIM905 [*] Consider using a list literal instead of `str.split`
    --> SIM905.py:173:1
@@ -1455,6 +1458,8 @@ SIM905 [*] Consider using a list literal instead of `str.split`
 172 | " a b c d ".rsplit(maxsplit=2)  # [" a b", "c", "d"]
 173 | "a  b".split(maxsplit=1)  # ["a", "b"]
     | ^^^^^^^^^^^^^^^^^^^^^^^^
+174 |
+175 | # https://github.com/astral-sh/ruff/issues/19610
     |
 help: Replace with list literal
 170 | # leading/trailing whitespace should not count towards maxsplit
@@ -1462,3 +1467,79 @@ help: Replace with list literal
 172 | " a b c d ".rsplit(maxsplit=2)  # [" a b", "c", "d"]
     - "a  b".split(maxsplit=1)  # ["a", "b"]
 173 + ["a", "b"]  # ["a", "b"]
+174 | 
+175 | # https://github.com/astral-sh/ruff/issues/19610
+176 | r"1" "\n".split("1")  # [r"", "\n"]
+
+SIM905 [*] Consider using a list literal instead of `str.split`
+   --> SIM905.py:176:1
+    |
+175 | # https://github.com/astral-sh/ruff/issues/19610
+176 | r"1" "\n".split("1")  # [r"", "\n"]
+    | ^^^^^^^^^^^^^^^^^^^^
+177 | r"" "\"".split("1")  # ['"']
+178 | r"1" """
+    |
+help: Replace with list literal
+173 | "a  b".split(maxsplit=1)  # ["a", "b"]
+174 | 
+175 | # https://github.com/astral-sh/ruff/issues/19610
+    - r"1" "\n".split("1")  # [r"", "\n"]
+176 + [r"", '\n']  # [r"", "\n"]
+177 | r"" "\"".split("1")  # ['"']
+178 | r"1" """
+179 | """.split("1")  # [r"", "\n"]
+
+SIM905 [*] Consider using a list literal instead of `str.split`
+   --> SIM905.py:177:1
+    |
+175 | # https://github.com/astral-sh/ruff/issues/19610
+176 | r"1" "\n".split("1")  # [r"", "\n"]
+177 | r"" "\"".split("1")  # ['"']
+    | ^^^^^^^^^^^^^^^^^^^
+178 | r"1" """
+179 | """.split("1")  # [r"", "\n"]
+    |
+help: Replace with list literal
+174 | 
+175 | # https://github.com/astral-sh/ruff/issues/19610
+176 | r"1" "\n".split("1")  # [r"", "\n"]
+    - r"" "\"".split("1")  # ['"']
+177 + [r'"']  # ['"']
+178 | r"1" """
+179 | """.split("1")  # [r"", "\n"]
+180 | r"\n" "\n'\"".split("1")  # ["\\n\n'\""]
+
+SIM905 [*] Consider using a list literal instead of `str.split`
+   --> SIM905.py:178:1
+    |
+176 |   r"1" "\n".split("1")  # [r"", "\n"]
+177 |   r"" "\"".split("1")  # ['"']
+178 | / r"1" """
+179 | | """.split("1")  # [r"", "\n"]
+    | |______________^
+180 |   r"\n" "\n'\"".split("1")  # ["\\n\n'\""]
+    |
+help: Replace with list literal
+175 | # https://github.com/astral-sh/ruff/issues/19610
+176 | r"1" "\n".split("1")  # [r"", "\n"]
+177 | r"" "\"".split("1")  # ['"']
+    - r"1" """
+    - """.split("1")  # [r"", "\n"]
+178 + [r"", '\n']  # [r"", "\n"]
+179 | r"\n" "\n'\"".split("1")  # ["\\n\n'\""]
+
+SIM905 [*] Consider using a list literal instead of `str.split`
+   --> SIM905.py:180:1
+    |
+178 | r"1" """
+179 | """.split("1")  # [r"", "\n"]
+180 | r"\n" "\n'\"".split("1")  # ["\\n\n'\""]
+    | ^^^^^^^^^^^^^^^^^^^^^^^^
+    |
+help: Replace with list literal
+177 | r"" "\"".split("1")  # ['"']
+178 | r"1" """
+179 | """.split("1")  # [r"", "\n"]
+    - r"\n" "\n'\"".split("1")  # ["\\n\n'\""]
+180 + ['\\n\n\'"']  # ["\\n\n'\""]