diff --git a/exercises/bob/.meta/description.md b/exercises/bob/.meta/description.md
deleted file mode 100644
index 1072139f..00000000
--- a/exercises/bob/.meta/description.md
+++ /dev/null
@@ -1,10 +0,0 @@
-Bob is a lackadaisical teenager. In conversation, his responses are very limited.
-
-Bob answers 'Sure.' if you ask him a question.
-
-He answers 'Whoa, chill out!' if you yell at him.
-
-He says 'Fine. Be that way!' if you address him without actually saying
-anything.
-
-He answers 'Whatever.' to anything else.
diff --git a/exercises/bob/README.md b/exercises/bob/README.md
index 3072e506..3c5af578 100644
--- a/exercises/bob/README.md
+++ b/exercises/bob/README.md
@@ -1,15 +1,19 @@
 # Bob
 
-Bob is a lackadaisical teenager. In conversation, his responses are very limited.
-
-Bob answers 'Sure.' if you ask him a question.
-
-He answers 'Whoa, chill out!' if you yell at him.
-
-He says 'Fine. Be that way!' if you address him without actually saying
-anything.
-
-He answers 'Whatever.' to anything else.
+Bob is a lackadaisical teenager. In conversation, his responses are very limited.
+
+Bob answers 'Sure.' if you ask him a question, such as "How are you?".
+
+He answers 'Whoa, chill out!' if you YELL AT HIM (in all capitals).
+
+He answers 'Calm down, I know what I'm doing!' if you yell a question at him.
+
+He says 'Fine. Be that way!' if you address him without actually saying
+anything.
+
+He answers 'Whatever.' to anything else.
+
+Bob's conversational partner is a purist when it comes to written communication and always follows normal rules regarding sentence punctuation in English.
 
 ## Getting Started
 
diff --git a/exercises/bob/bob_test.cpp b/exercises/bob/bob_test.cpp
index 9924fe81..acde7567 100644
--- a/exercises/bob/bob_test.cpp
+++ b/exercises/bob/bob_test.cpp
@@ -1,6 +1,8 @@
 #include "bob.h"
 #include "test/catch.hpp"
 
+// Bob exercise test case data version 1.4.0
+
 TEST_CASE("stating_something")
 {
     REQUIRE("Whatever." == bob::hey("Tom-ay-to, tom-aaaah-to."));
@@ -12,11 +14,26 @@ TEST_CASE("shouting")
     REQUIRE("Whoa, chill out!" == bob::hey("WATCH OUT!"));
 }
 
+TEST_CASE("shouting_gibberish")
+{
+    REQUIRE("Whoa, chill out!" == bob::hey("FCECDFCAAB"));
+}
+
 TEST_CASE("asking_a_question")
 {
     REQUIRE("Sure." == bob::hey("Does this cryogenic chamber make me look fat?"));
 }
 
+TEST_CASE("asking_a_numeric_question")
+{
+    REQUIRE("Sure." == bob::hey("You are, what, like 15?"));
+}
+
+TEST_CASE("asking_gibberish")
+{
+    REQUIRE("Sure." == bob::hey("fffbbcbeab?"));
+}
+
 TEST_CASE("talking_forcefully")
 {
     REQUIRE("Whatever." == bob::hey("Let's go make out behind the gym!"));
@@ -29,7 +46,7 @@ TEST_CASE("using_acronyms_in_regular_speech")
 
 TEST_CASE("forceful_questions")
 {
-    REQUIRE("Whoa, chill out!" == bob::hey("WHAT THE HELL WERE YOU THINKING?"));
+    REQUIRE("Calm down, I know what I'm doing!" == bob::hey("WHAT THE HELL WERE YOU THINKING?"));
 }
 
 TEST_CASE("shouting_numbers")
@@ -37,12 +54,12 @@ TEST_CASE("shouting_numbers")
     REQUIRE("Whoa, chill out!" == bob::hey("1, 2, 3 GO!"));
 }
 
-TEST_CASE("only_numbers")
+TEST_CASE("no_letters")
 {
     REQUIRE("Whatever." == bob::hey("1, 2, 3"));
 }
 
-TEST_CASE("question_with_only_numbers")
+TEST_CASE("question_with_no_letters")
 {
     REQUIRE("Sure." == bob::hey("4?"));
 }
@@ -54,22 +71,22 @@ TEST_CASE("shouting_with_special_characters")
 
 TEST_CASE("shouting_with_no_exclamation_mark")
 {
-    REQUIRE("Whoa, chill out!" == bob::hey("I HATE YOU"));
+    REQUIRE("Whoa, chill out!" == bob::hey("I HATE THE DMV"));
 }
 
 TEST_CASE("statement_containing_question_mark")
 {
-    REQUIRE("Whatever." == bob::hey("Ending with a ? means a question."));
+    REQUIRE("Whatever." == bob::hey("Ending with ? means a question."));
 }
 
-TEST_CASE("prattling_on")
+TEST_CASE("non_letters_with_question")
 {
-    REQUIRE("Sure." == bob::hey("Wait! Hang on.  Are you going to be OK?"));
+    REQUIRE("Sure." == bob::hey(":) ?"));
 }
 
-TEST_CASE("question_with_trailing_whitespace")
+TEST_CASE("prattling_on")
 {
-    REQUIRE("Sure." == bob::hey("Are you ok? "));
+    REQUIRE("Sure." == bob::hey("Wait! Hang on. Are you going to be OK?"));
 }
 
 TEST_CASE("silence")
@@ -79,11 +96,36 @@ TEST_CASE("silence")
 
 TEST_CASE("prolonged_silence")
 {
-    REQUIRE("Fine. Be that way!" == bob::hey("   "));
+    REQUIRE("Fine. Be that way!" == bob::hey("          "));
+}
+
+TEST_CASE("alternate_silence")
+{
+    REQUIRE("Fine. Be that way!" == bob::hey("\t\t\t\t\t\t\t\t\t\t"));
+}
+
+TEST_CASE("multiple_line_question")
+{
+	REQUIRE("Whatever." == bob::hey("\nDoes this cryogenic chamber make me look fat?\nNo."));
+}
+
+TEST_CASE("starting_with_whitespace")
+{
+	REQUIRE("Whatever." == bob::hey("         hmmmmmmm..."));
+}
+
+TEST_CASE("ending_with_whitespace")
+{
+	REQUIRE("Sure." == bob::hey("Okay if like my  spacebar  quite a bit?   "));
+}
+
+TEST_CASE("other_whitespace")
+{
+	REQUIRE("Fine. Be that way!" == bob::hey("\n\r \t"));
 }
 
-TEST_CASE("not_all_silence")
+TEST_CASE("non_question_ending_with_whitespace")
 {
-	REQUIRE("Whatever." == bob::hey(" A bit of silence can be nice.  "));
+	REQUIRE("Whatever." == bob::hey("This is a statement ending with whitespace      "));
 }
 #endif
diff --git a/exercises/bob/example.cpp b/exercises/bob/example.cpp
index 793f3e71..563f8178 100644
--- a/exercises/bob/example.cpp
+++ b/exercises/bob/example.cpp
@@ -14,10 +14,10 @@ string trim_copy(string const& s)
 {
     string cpy(s);
     // Trim front
-    while (!cpy.empty() && cpy.front() == ' ')
+    while (!cpy.empty() && std::isspace(static_cast<unsigned char>(cpy.front())))
         cpy.erase(cpy.begin());
     // Trim back
-    while (!cpy.empty() && cpy.back() == ' ')
+    while (!cpy.empty() && std::isspace(static_cast<unsigned char>(cpy.back())))
         cpy.pop_back();
     return cpy;
 }
@@ -52,7 +52,7 @@ bool is_silence(string const& text)
     return trim_copy(text).length() == 0;
 }
 
-}
+} // anonymous namespace
 
 string hey(string const& text)
 {
@@ -60,6 +60,8 @@ string hey(string const& text)
         return "Fine. Be that way!";
     }
     if (is_shouting(text)) {
+        if (is_question(text))
+            return "Calm down, I know what I'm doing!";
         return "Whoa, chill out!";
     }
     if (is_question(text)) {
@@ -68,4 +70,4 @@ string hey(string const& text)
     return "Whatever.";
 }
 
-}
+} // namespace bob