diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_todos/TD003.py b/crates/ruff_linter/resources/test/fixtures/flake8_todos/TD003.py
index 0423e5f481..e41dbfcbc0 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_todos/TD003.py
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_todos/TD003.py
@@ -42,17 +42,17 @@ def foo(x):
 
 # TODO: here's a TODO on the last line with no link
 
+# Valid Jira-style patterns (should pass)
 # TODO: Move this part to the other place RFFU-6877
-
 # TODO: PROJ-123 Another Jira-style example
-
-# TODO: Valid Jira-style issue IDs (should pass)
 # TODO: Fix bug ABC-123
 # TODO: Implement feature XYZ-456
 # TODO: Update documentation DEF-789
 # TODO: Refactor code GHI-101112
+# TODO: Fix this (AIRFLOW-123)
+# TODO: Update config (SUPERSET-456)
 
-# TODO: Invalid patterns that should still trigger TD003 (should fail)
+# Invalid patterns that should still trigger TD003 (should fail)
 # TODO: Single letter project key A-1
 # TODO: No hyphen pattern ABC123
 # TODO: Lowercase project key abc-123
@@ -61,3 +61,5 @@ def foo(x):
 # TODO: Number before letters 123-ABC
 # TODO: Multiple hyphens ABC-123-456
 # TODO: Empty project key -123
+# TODO: This is about PROJ-123 server config (ID in middle of sentence)
+# TODO: Working on PROJ-123 and PROJ-456 (multiple IDs)
diff --git a/crates/ruff_linter/src/rules/flake8_todos/rules/todos.rs b/crates/ruff_linter/src/rules/flake8_todos/rules/todos.rs
index 8334d9de81..77f97d87d4 100644
--- a/crates/ruff_linter/src/rules/flake8_todos/rules/todos.rs
+++ b/crates/ruff_linter/src/rules/flake8_todos/rules/todos.rs
@@ -248,7 +248,9 @@ static ISSUE_LINK_TODO_LINE_REGEX_SET: LazyLock<RegexSet> = LazyLock::new(|| {
     RegexSet::new([
         r"\s*(http|https)://.*", // issue link
         r"\s*#\d+.*",            // issue code - like "#003"
-        r"\s*[A-Z]{2,}-\d+.*",   // Jira-style issue code - like "RFFU-6877"
+        r"\s*[A-Z]{2,}-\d+\s*$", // Jira-style issue code at end of line - like "RFFU-6877"
+        r"\s*[A-Z]{2,}-\d+\s",   // Jira-style issue code followed by space - like "RFFU-6877 "
+        r"\s*\([A-Z]{2,}-\d+\)", // Jira-style issue code in parentheses - like "(RFFU-6877)"
     ])
     .unwrap()
 });
diff --git a/crates/ruff_linter/src/rules/flake8_todos/snapshots/ruff_linter__rules__flake8_todos__tests__missing-todo-link_TD003.py.snap b/crates/ruff_linter/src/rules/flake8_todos/snapshots/ruff_linter__rules__flake8_todos__tests__missing-todo-link_TD003.py.snap
index 6bd240fac2..47714f4ce9 100644
--- a/crates/ruff_linter/src/rules/flake8_todos/snapshots/ruff_linter__rules__flake8_todos__tests__missing-todo-link_TD003.py.snap
+++ b/crates/ruff_linter/src/rules/flake8_todos/snapshots/ruff_linter__rules__flake8_todos__tests__missing-todo-link_TD003.py.snap
@@ -62,35 +62,13 @@ TD003 Missing issue link for this TODO
 43 | # TODO: here's a TODO on the last line with no link
    |   ^^^^
 44 |
-45 | # TODO: Move this part to the other place RFFU-6877
-   |
-
-TD003 Missing issue link for this TODO
-  --> TD003.py:49:3
-   |
-47 | # TODO: PROJ-123 Another Jira-style example
-48 |
-49 | # TODO: Valid Jira-style issue IDs (should pass)
-   |   ^^^^
-50 | # TODO: Fix bug ABC-123
-51 | # TODO: Implement feature XYZ-456
-   |
-
-TD003 Missing issue link for this TODO
-  --> TD003.py:55:3
-   |
-53 | # TODO: Refactor code GHI-101112
-54 |
-55 | # TODO: Invalid patterns that should still trigger TD003 (should fail)
-   |   ^^^^
-56 | # TODO: Single letter project key A-1
-57 | # TODO: No hyphen pattern ABC123
+45 | # Valid Jira-style patterns (should pass)
    |
 
 TD003 Missing issue link for this TODO
   --> TD003.py:56:3
    |
-55 | # TODO: Invalid patterns that should still trigger TD003 (should fail)
+55 | # Invalid patterns that should still trigger TD003 (should fail)
 56 | # TODO: Single letter project key A-1
    |   ^^^^
 57 | # TODO: No hyphen pattern ABC123
@@ -100,7 +78,7 @@ TD003 Missing issue link for this TODO
 TD003 Missing issue link for this TODO
   --> TD003.py:57:3
    |
-55 | # TODO: Invalid patterns that should still trigger TD003 (should fail)
+55 | # Invalid patterns that should still trigger TD003 (should fail)
 56 | # TODO: Single letter project key A-1
 57 | # TODO: No hyphen pattern ABC123
    |   ^^^^
@@ -152,6 +130,17 @@ TD003 Missing issue link for this TODO
 63 | # TODO: Empty project key -123
    |
 
+TD003 Missing issue link for this TODO
+  --> TD003.py:62:3
+   |
+60 | # TODO: Just a random word with hyphen and number random-123
+61 | # TODO: Number before letters 123-ABC
+62 | # TODO: Multiple hyphens ABC-123-456
+   |   ^^^^
+63 | # TODO: Empty project key -123
+64 | # TODO: This is about PROJ-123 server config (ID in middle of sentence)
+   |
+
 TD003 Missing issue link for this TODO
   --> TD003.py:63:3
    |
@@ -159,4 +148,6 @@ TD003 Missing issue link for this TODO
 62 | # TODO: Multiple hyphens ABC-123-456
 63 | # TODO: Empty project key -123
    |   ^^^^
+64 | # TODO: This is about PROJ-123 server config (ID in middle of sentence)
+65 | # TODO: Working on PROJ-123 and PROJ-456 (multiple IDs)
    |