diff --git a/resources/test/fixtures/pydocstyle/D.py b/resources/test/fixtures/pydocstyle/D.py
index 113018fcf3..30c63e8360 100644
--- a/resources/test/fixtures/pydocstyle/D.py
+++ b/resources/test/fixtures/pydocstyle/D.py
@@ -571,3 +571,11 @@ def multiline_trailing_and_leading_space():
     """
 
     pass
+
+
+@expect('D210: No whitespaces allowed surrounding docstring text')
+@expect("D400: First line should end with a period (not '\"')")
+@expect("D415: First line should end with a period, question mark, "
+        "or exclamation point (not '\"')")
+def endswith_quote():
+    """Whitespace at the end, but also a quote" """
diff --git a/src/pydocstyle/plugins.rs b/src/pydocstyle/plugins.rs
index 6eb4a9d81c..394a05f774 100644
--- a/src/pydocstyle/plugins.rs
+++ b/src/pydocstyle/plugins.rs
@@ -633,17 +633,25 @@ pub fn no_surrounding_whitespace(checker: &mut Checker, definition: &Definition)
                 .chain(constants::SINGLE_QUOTE_PREFIXES)
             {
                 if first_line.starts_with(pattern) {
-                    check.amend(Fix::replacement(
-                        trimmed.to_string(),
-                        Location::new(
-                            docstring.location.row(),
-                            docstring.location.column() + pattern.len(),
-                        ),
-                        Location::new(
-                            docstring.location.row(),
-                            docstring.location.column() + pattern.len() + line.chars().count(),
-                        ),
-                    ));
+                    if let Some(quote) = pattern.chars().last() {
+                        // If removing whitespace would lead to an invalid string of quote
+                        // characters, avoid applying the fix.
+                        if !trimmed.ends_with(quote) {
+                            check.amend(Fix::replacement(
+                                trimmed.to_string(),
+                                Location::new(
+                                    docstring.location.row(),
+                                    docstring.location.column() + pattern.len(),
+                                ),
+                                Location::new(
+                                    docstring.location.row(),
+                                    docstring.location.column()
+                                        + pattern.len()
+                                        + line.chars().count(),
+                                ),
+                            ));
+                        }
+                    }
                     break;
                 }
             }
diff --git a/src/pydocstyle/snapshots/ruff__pydocstyle__tests__D210_D.py.snap b/src/pydocstyle/snapshots/ruff__pydocstyle__tests__D210_D.py.snap
index c451b9cd79..bef21772fe 100644
--- a/src/pydocstyle/snapshots/ruff__pydocstyle__tests__D210_D.py.snap
+++ b/src/pydocstyle/snapshots/ruff__pydocstyle__tests__D210_D.py.snap
@@ -47,4 +47,12 @@ expression: checks
     end_location:
       row: 299
       column: 36
+- kind: NoSurroundingWhitespace
+  location:
+    row: 581
+    column: 4
+  end_location:
+    row: 581
+    column: 51
+  fix: ~
 
diff --git a/src/pydocstyle/snapshots/ruff__pydocstyle__tests__D400_D.py.snap b/src/pydocstyle/snapshots/ruff__pydocstyle__tests__D400_D.py.snap
index b4c7f9f41d..af29dfeb26 100644
--- a/src/pydocstyle/snapshots/ruff__pydocstyle__tests__D400_D.py.snap
+++ b/src/pydocstyle/snapshots/ruff__pydocstyle__tests__D400_D.py.snap
@@ -106,4 +106,12 @@ expression: checks
     row: 520
     column: 32
   fix: ~
+- kind: EndsInPeriod
+  location:
+    row: 581
+    column: 4
+  end_location:
+    row: 581
+    column: 51
+  fix: ~
 
diff --git a/src/pydocstyle/snapshots/ruff__pydocstyle__tests__D415_D.py.snap b/src/pydocstyle/snapshots/ruff__pydocstyle__tests__D415_D.py.snap
index c8c3d95e90..ff70dcc778 100644
--- a/src/pydocstyle/snapshots/ruff__pydocstyle__tests__D415_D.py.snap
+++ b/src/pydocstyle/snapshots/ruff__pydocstyle__tests__D415_D.py.snap
@@ -98,4 +98,12 @@ expression: checks
     row: 520
     column: 32
   fix: ~
+- kind: EndsInPunctuation
+  location:
+    row: 581
+    column: 4
+  end_location:
+    row: 581
+    column: 51
+  fix: ~