diff --git a/core/src/main/java/com/google/googlejavaformat/java/StringWrapper.java b/core/src/main/java/com/google/googlejavaformat/java/StringWrapper.java
index 063843622..c0f16e9b5 100644
--- a/core/src/main/java/com/google/googlejavaformat/java/StringWrapper.java
+++ b/core/src/main/java/com/google/googlejavaformat/java/StringWrapper.java
@@ -239,9 +239,10 @@ static int hasEscapedNewlineAt(String input, int idx) {
    * @param separator the line separator
    * @param columnLimit the number of columns to wrap at
    * @param startColumn the column position of the beginning of the original text
-   * @param trailing extra space to leave after the last line
-   * @param components the text to reflow
-   * @param first0 true if the text includes the beginning of its enclosing concat chain, i.e. a
+   * @param trailing extra space to leave after the last line, to accommodate a ; or )
+   * @param components the text to reflow. This is a list of “words” of a single literal. Its first
+   *     and last quotes have been stripped
+   * @param first0 true if the text includes the beginning of its enclosing concat chain
    */
   private static String reflow(
       String separator,
@@ -251,7 +252,7 @@ private static String reflow(
       ImmutableList<String> components,
       boolean first0) {
     // We have space between the start column and the limit to output the first line.
-    // Reserve two spaces for the quotes.
+    // Reserve two spaces for the start and end quotes.
     int width = columnLimit - startColumn - 2;
     Deque<String> input = new ArrayDeque<>(components);
     List<String> lines = new ArrayList<>();
@@ -259,10 +260,13 @@ private static String reflow(
     while (!input.isEmpty()) {
       int length = 0;
       List<String> line = new ArrayList<>();
+      // If we know this is going to be the last line, then remove a bit of width to account for the
+      // trailing characters.
       if (input.stream().mapToInt(String::length).sum() <= width) {
+        // This isn’t quite optimal, but arguably good enough. See b/179561701
         width -= trailing;
       }
-      while (!input.isEmpty() && (length <= 4 || (length + input.peekFirst().length()) < width)) {
+      while (!input.isEmpty() && (length <= 4 || (length + input.peekFirst().length()) <= width)) {
         String text = input.removeFirst();
         line.add(text);
         length += text.length();
diff --git a/core/src/test/java/com/google/googlejavaformat/java/FormatterIntegrationTest.java b/core/src/test/java/com/google/googlejavaformat/java/FormatterIntegrationTest.java
index 44ba63925..fdcf6f8a8 100644
--- a/core/src/test/java/com/google/googlejavaformat/java/FormatterIntegrationTest.java
+++ b/core/src/test/java/com/google/googlejavaformat/java/FormatterIntegrationTest.java
@@ -125,7 +125,9 @@ public FormatterIntegrationTest(String name, String input, String expected) {
   @Test
   public void format() {
     try {
-      String output = new Formatter().formatSource(input);
+      Formatter formatter = new Formatter();
+      String output = formatter.formatSource(input);
+      output = StringWrapper.wrap(output, formatter);
       assertEquals("bad output for " + name, expected, output);
     } catch (FormatterException e) {
       fail(String.format("Formatter crashed on %s: %s", name, e.getMessage()));
diff --git a/core/src/test/java/com/google/googlejavaformat/java/MainTest.java b/core/src/test/java/com/google/googlejavaformat/java/MainTest.java
index fa23486fd..a7e10fee7 100644
--- a/core/src/test/java/com/google/googlejavaformat/java/MainTest.java
+++ b/core/src/test/java/com/google/googlejavaformat/java/MainTest.java
@@ -525,8 +525,8 @@ public void reflowLongStrings() throws Exception {
       "class T {",
       "  String s =",
       "      \"one long incredibly unbroken sentence moving from topic to topic so that no one had"
-          + " a\"",
-      "          + \" chance to interrupt\";",
+          + " a chance\"",
+      "          + \" to interrupt\";",
       "}",
       "",
     };
diff --git a/core/src/test/resources/com/google/googlejavaformat/java/testdata/B173808510.input b/core/src/test/resources/com/google/googlejavaformat/java/testdata/B173808510.input
new file mode 100644
index 000000000..e3e849399
--- /dev/null
+++ b/core/src/test/resources/com/google/googlejavaformat/java/testdata/B173808510.input
@@ -0,0 +1,8 @@
+class B173808510 {
+  // b/173808510
+  @FlagSpec(
+      name = "myFlag",
+      help =
+          "areallyreallyreallyreallyreallyreallyreallyreallyreallyreallyreallyreallyloongword word1 word2")
+  Flag<Integer> dummy = null;
+}
diff --git a/core/src/test/resources/com/google/googlejavaformat/java/testdata/B173808510.output b/core/src/test/resources/com/google/googlejavaformat/java/testdata/B173808510.output
new file mode 100644
index 000000000..45a939efb
--- /dev/null
+++ b/core/src/test/resources/com/google/googlejavaformat/java/testdata/B173808510.output
@@ -0,0 +1,9 @@
+class B173808510 {
+  // b/173808510
+  @FlagSpec(
+      name = "myFlag",
+      help =
+          "areallyreallyreallyreallyreallyreallyreallyreallyreallyreallyreallyreallyloongword word1"
+              + " word2")
+  Flag<Integer> dummy = null;
+}
diff --git a/core/src/test/resources/com/google/googlejavaformat/java/testdata/LiteralReflow.input b/core/src/test/resources/com/google/googlejavaformat/java/testdata/LiteralReflow.input
new file mode 100644
index 000000000..2aa4de330
--- /dev/null
+++ b/core/src/test/resources/com/google/googlejavaformat/java/testdata/LiteralReflow.input
@@ -0,0 +1,44 @@
+class LiteralReflow {
+  static class TestLineBreak {
+    String doesNotBreakAt100 = "A very long long long long long long long long long loong sentence";
+    String breaksAt101 = "A very long long long long long long long long long long loooong sentence";
+  }
+
+  static class TestReflowLimit {
+    String doesNotReflowAt100 =
+        "A very long long long long long long long long long long long long long looooong sentence";
+    String reflowsWhenLongerThan100 =
+        "A very long long long long long long long long long long long long long long long sentence";
+  }
+
+  static class TestReflowLocation {
+    String accommodatesWordsUpTo100 =
+        "A very long long long long long long long long long long long long long long long looooong sentence";
+    String breaksBeforeWordsReach101 =
+        "A very long long long long long long long long long long long long long long long loooooong sentence";
+  }
+
+  static class Test2LineReflowLimit {
+    String doesNotReflowEitherLinesAt100 =
+        "A very long long long long long long long long long long long long long looooong sentence. And a second very long long long long long long long long long long loong sentence";
+    String reflowsLastLineAt101 =
+        "A very long long long long long long long long long long long long long looooong sentence. And a second very long long long long long long long long long long looong sentence";
+  }
+
+  static class TestWithTrailingCharacters {
+    String fitsLastLineUpTo100WithTrailingCharacters =
+        f(
+            f(
+                "A very long long long long long long long long long long long long loong sentence. And a second very long long long long long long long long loong sentence"));
+    String reflowsLastLineToAccommodateTrailingCharacters =
+        f(
+            f(
+                "A very long long long long long long long long long long long long loong sentence. And a second very long long long long long long long long looong sentence"));
+    // Tests an off-by-one issue, but see b/179561701 for a similar issue that is not yet fixed
+    String doesNotOverTriggerLastLineReflow =
+        f(
+            f(
+                "A very long long long long long long long long long long long long loong sentence."
+                    + " And a second very loong sentence with trailing a a a a a a a a a a a a a a a"));
+  }
+}
diff --git a/core/src/test/resources/com/google/googlejavaformat/java/testdata/LiteralReflow.output b/core/src/test/resources/com/google/googlejavaformat/java/testdata/LiteralReflow.output
new file mode 100644
index 000000000..50ed7bda1
--- /dev/null
+++ b/core/src/test/resources/com/google/googlejavaformat/java/testdata/LiteralReflow.output
@@ -0,0 +1,55 @@
+class LiteralReflow {
+  static class TestLineBreak {
+    String doesNotBreakAt100 = "A very long long long long long long long long long loong sentence";
+    String breaksAt101 =
+        "A very long long long long long long long long long long loooong sentence";
+  }
+
+  static class TestReflowLimit {
+    String doesNotReflowAt100 =
+        "A very long long long long long long long long long long long long long looooong sentence";
+    String reflowsWhenLongerThan100 =
+        "A very long long long long long long long long long long long long long long long"
+            + " sentence";
+  }
+
+  static class TestReflowLocation {
+    String accommodatesWordsUpTo100 =
+        "A very long long long long long long long long long long long long long long long looooong"
+            + " sentence";
+    String breaksBeforeWordsReach101 =
+        "A very long long long long long long long long long long long long long long long"
+            + " loooooong sentence";
+  }
+
+  static class Test2LineReflowLimit {
+    String doesNotReflowEitherLinesAt100 =
+        "A very long long long long long long long long long long long long long looooong sentence."
+            + " And a second very long long long long long long long long long long loong sentence";
+    String reflowsLastLineAt101 =
+        "A very long long long long long long long long long long long long long looooong sentence."
+            + " And a second very long long long long long long long long long long looong"
+            + " sentence";
+  }
+
+  static class TestWithTrailingCharacters {
+    String fitsLastLineUpTo100WithTrailingCharacters =
+        f(
+            f(
+                "A very long long long long long long long long long long long long loong sentence."
+                    + " And a second very long long long long long long long long loong sentence"));
+    String reflowsLastLineToAccommodateTrailingCharacters =
+        f(
+            f(
+                "A very long long long long long long long long long long long long loong sentence."
+                    + " And a second very long long long long long long long long looong"
+                    + " sentence"));
+    // Tests an off-by-one issue, but see b/179561701 for a similar issue that is not yet fixed
+    String doesNotOverTriggerLastLineReflow =
+        f(
+            f(
+                "A very long long long long long long long long long long long long loong sentence."
+                    + " And a second very loong sentence with trailing a a a a a a a a a a a a a a"
+                    + " a"));
+  }
+}