diff --git a/docs/metadata/data_structures/location.rst b/docs/metadata/data_structures/location.rst
index 97b66065..65d0b4e4 100644
--- a/docs/metadata/data_structures/location.rst
+++ b/docs/metadata/data_structures/location.rst
@@ -22,7 +22,7 @@ The scalar form is simply the value of the map form's ``link`` key. Using the sc
 Equality
 --------
 
-Two location data structures are equal if the lowercased values of their ``link`` keys are identical.
+Two location data structures are equal if the values of their ``link`` keys are identical.
 
 Examples
 --------
diff --git a/docs/metadata/data_structures/message.rst b/docs/metadata/data_structures/message.rst
index 3a9e6a36..712bc5fd 100644
--- a/docs/metadata/data_structures/message.rst
+++ b/docs/metadata/data_structures/message.rst
@@ -57,12 +57,8 @@ If a message's ``content`` value is a string, the message will use the string as
 Equality
 --------
 
-The equality of two message data structures is determined by comparing the values of their ``content`` keys. As the values of the keys can be different types, a comparison value is selected for each message using the following logic:
-
-* If a value's type is a localised content list, then the English content string in that list is selected as the comparison value.
-* If a value's type is a string, then that string is selected as the comparison value.
-
-The two message data structures are then equal if their lowercased comparison values are identical.
+The equality of two message data structures is determined by comparing the values of their ``content`` keys. If a content key is a string, it is treated as a localised content list
+containing a single English-language string. The two message data structures are then equal if their localised content lists are identical.
 
 Examples
 --------
diff --git a/docs/metadata/data_structures/tag.rst b/docs/metadata/data_structures/tag.rst
index 56d69896..468f3623 100644
--- a/docs/metadata/data_structures/tag.rst
+++ b/docs/metadata/data_structures/tag.rst
@@ -22,7 +22,7 @@ The scalar form is simply the value of the map form's ``name`` key. Using the sc
 Equality
 --------
 
-Two tag data structures are equal if the lowercased values of their ``name`` keys are identical.
+Two tag data structures are equal if the values of their ``name`` keys are identical.
 
 Examples
 --------
diff --git a/include/loot/metadata/location.h b/include/loot/metadata/location.h
index 8e343b2c..7326d61d 100644
--- a/include/loot/metadata/location.h
+++ b/include/loot/metadata/location.h
@@ -54,15 +54,14 @@ public:
   /**
    * A less-than operator implemented with no semantics so that Location objects
    * can be stored in sets.
-   * @returns True if this Location's URL is case-insensitively
-   *          lexicographically less than the given Location's URL, false
-   *          otherwise.
+   * @returns True if this Location's URL string is lexicographically less than
+   *          the given Location's URL string, false otherwise.
    */
   LOOT_API bool operator<(const Location& rhs) const;
 
   /**
    * Check if two Location objects are equal by comparing their URLs.
-   * @returns True if the URLs are case-insensitively equal, false otherwise.
+   * @returns True if the URL strings are equal, false otherwise.
    */
   LOOT_API bool operator==(const Location& rhs) const;
 
diff --git a/include/loot/metadata/message.h b/include/loot/metadata/message.h
index e27dfa2e..b282ba45 100644
--- a/include/loot/metadata/message.h
+++ b/include/loot/metadata/message.h
@@ -79,11 +79,8 @@ public:
   /**
    * A less-than operator implemented with no semantics so that Message objects
    * can be stored in sets.
-   * @returns If both messages have content, returns true if this Message's
-   *          English text is case-insensitively lexicographically less than the
-   *          given Message's English text, and false otherwise.
-   *          Otherwise returns true if this Message has no content, and false
-   *          otherwise.
+   * @returns Returns true if this Message's content is lexicographically less
+   *          than the given Message's content, and false otherwise.
    */
   LOOT_API bool operator<(const Message& rhs) const;
 
diff --git a/include/loot/metadata/message_content.h b/include/loot/metadata/message_content.h
index c9c7e430..238a01b1 100644
--- a/include/loot/metadata/message_content.h
+++ b/include/loot/metadata/message_content.h
@@ -73,15 +73,14 @@ public:
   /**
    * A less-than operator implemented with no semantics so that MessageContent
    * objects can be stored in sets.
-   * @returns True if this MessageContent's text is case-insensitively
-   *          lexicographically less than the given MessageContent's text, false
-   *          otherwise.
+   * @returns True if this MessageContent's text is lexicographically less than
+   *          the given MessageContent's text, false otherwise.
    */
   LOOT_API bool operator<(const MessageContent& rhs) const;
 
   /**
    * Check if two MessageContent objects are equal by comparing their texts.
-   * @returns True if the texts are case-insensitively equal, false otherwise.
+   * @returns True if the texts are equal, false otherwise.
    */
   LOOT_API bool operator==(const MessageContent& rhs) const;
 
diff --git a/include/loot/metadata/tag.h b/include/loot/metadata/tag.h
index 97001243..f3b9fdc4 100644
--- a/include/loot/metadata/tag.h
+++ b/include/loot/metadata/tag.h
@@ -62,17 +62,15 @@ public:
    * can be stored in sets.
    * @returns True if this Tag is suggested for addition and the other is not.
    *          If both Tags are suggested for addition or both are suggested for
-   *          removal, returns true if this Tag's name is case-insensitively
-   *          lexicographically less than the given Tag's name, false
-   *          otherwise.
+   *          removal, returns true if this Tag's name is lexicographically less
+   *          than the given Tag's name, false otherwise.
    */
   LOOT_API bool operator<(const Tag& rhs) const;
 
   /**
    * Check if two Tag objects are equal.
    * @returns True if both Tags are suggested for addition or both are suggested
-   *          for removal, and the Tag names are case-insensitively equal, false
-   *          otherwise.
+   *          for removal, and the Tag names are equal, false otherwise.
    */
   LOOT_API bool operator==(const Tag& rhs) const;
 
diff --git a/src/api/metadata/location.cpp b/src/api/metadata/location.cpp
index b2410ba3..e2416a90 100644
--- a/src/api/metadata/location.cpp
+++ b/src/api/metadata/location.cpp
@@ -24,8 +24,6 @@
 
 #include "loot/metadata/location.h"
 
-#include <boost/algorithm/string.hpp>
-
 namespace loot {
 Location::Location() {}
 
@@ -34,11 +32,11 @@ Location::Location(const std::string& url, const std::string& name) :
     name_(name) {}
 
 bool Location::operator<(const Location& rhs) const {
-  return boost::ilexicographical_compare(url_, rhs.GetURL());
+  return url_ < rhs.url_;
 }
 
 bool Location::operator==(const Location& rhs) const {
-  return boost::iequals(url_, rhs.GetURL());
+  return url_ == rhs.url_;
 }
 
 std::string Location::GetURL() const { return url_; }
diff --git a/src/api/metadata/message.cpp b/src/api/metadata/message.cpp
index b25ffa4d..0a130068 100644
--- a/src/api/metadata/message.cpp
+++ b/src/api/metadata/message.cpp
@@ -59,18 +59,11 @@ Message::Message(const MessageType type,
 }
 
 bool Message::operator<(const Message& rhs) const {
-  if (!content_.empty() && !rhs.GetContent().empty())
-    return boost::ilexicographical_compare(
-        GetContent(MessageContent::defaultLanguage).GetText(),
-        rhs.GetContent(MessageContent::defaultLanguage).GetText());
-  else if (content_.empty() && !rhs.GetContent().empty())
-    return true;
-  else
-    return false;
+  return content_ < rhs.GetContent();
 }
 
 bool Message::operator==(const Message& rhs) const {
-  return (content_ == rhs.GetContent());
+  return content_ == rhs.GetContent();
 }
 
 MessageType Message::GetType() const { return type_; }
diff --git a/src/api/metadata/message_content.cpp b/src/api/metadata/message_content.cpp
index 1454dd7b..019e0fd8 100644
--- a/src/api/metadata/message_content.cpp
+++ b/src/api/metadata/message_content.cpp
@@ -41,11 +41,11 @@ std::string MessageContent::GetText() const { return text_; }
 std::string MessageContent::GetLanguage() const { return language_; }
 
 bool MessageContent::operator<(const MessageContent& rhs) const {
-  return boost::ilexicographical_compare(text_, rhs.GetText());
+  return text_ < rhs.text_;
 }
 
 bool MessageContent::operator==(const MessageContent& rhs) const {
-  return (boost::iequals(text_, rhs.GetText()));
+  return text_ == rhs.text_;
 }
 MessageContent MessageContent::Choose(const std::vector<MessageContent> content,
                                       const std::string& language) {
diff --git a/src/api/metadata/tag.cpp b/src/api/metadata/tag.cpp
index 0a684775..93440a02 100644
--- a/src/api/metadata/tag.cpp
+++ b/src/api/metadata/tag.cpp
@@ -38,14 +38,14 @@ Tag::Tag(const std::string& tag,
 
 bool Tag::operator<(const Tag& rhs) const {
   if (addTag_ != rhs.IsAddition())
-    return (addTag_ && !rhs.IsAddition());
+    return addTag_ && !rhs.IsAddition();
   else
-    return boost::ilexicographical_compare(GetName(), rhs.GetName());
+    return GetName() < rhs.GetName();
 }
 
 bool Tag::operator==(const Tag& rhs) const {
-  return (addTag_ == rhs.IsAddition() &&
-          boost::iequals(GetName(), rhs.GetName()));
+  return addTag_ == rhs.IsAddition() &&
+          GetName() == rhs.GetName();
 }
 
 bool Tag::IsAddition() const { return addTag_; }
diff --git a/src/tests/api/internals/metadata/location_test.h b/src/tests/api/internals/metadata/location_test.h
index 6add8f00..806b1d7c 100644
--- a/src/tests/api/internals/metadata/location_test.h
+++ b/src/tests/api/internals/metadata/location_test.h
@@ -47,11 +47,16 @@ TEST(Location, stringsConstructorShouldStoreGivenStrings) {
   EXPECT_EQ("example", location.GetName());
 }
 
-TEST(Location, locationsWithCaseInsensitiveEqualUrlsShouldBeEqual) {
+TEST(Location, locationsWithCaseSensitiveEqualUrlsShouldBeEqual) {
   Location location1("http://www.example.com", "example1");
-  Location location2("HTTP://WWW.EXAMPLE.COM", "example2");
+  Location location2("http://www.example.com", "example2");
 
   EXPECT_TRUE(location1 == location2);
+
+  location1 = Location("http://www.example.com");
+  location2 = Location("HTTP://WWW.EXAMPLE.COM");
+
+  EXPECT_FALSE(location1 == location2);
 }
 
 TEST(Location, locationsWithDifferentUrlsShouldBeUnequal) {
@@ -62,13 +67,19 @@ TEST(Location, locationsWithDifferentUrlsShouldBeUnequal) {
 }
 
 TEST(Location,
-     lessThanOperatorShouldUseCaseInsensitiveLexicographicalUrlComparison) {
+     lessThanOperatorShouldUseCaseSensitiveLexicographicalUrlComparison) {
   Location location1("http://www.example.com", "example1");
-  Location location2("HTTP://WWW.EXAMPLE.COM", "example2");
+  Location location2("http://www.example.com", "example2");
 
   EXPECT_FALSE(location1 < location2);
   EXPECT_FALSE(location2 < location1);
 
+  location1 = Location("http://www.example.com");
+  location2 = Location("HTTP://WWW.EXAMPLE.COM");
+
+  EXPECT_FALSE(location1 < location2);
+  EXPECT_TRUE(location2 < location1);
+
   location1 = Location("http://www.example1.com");
   location2 = Location("http://www.example2.com");
 
diff --git a/src/tests/api/internals/metadata/message_content_test.h b/src/tests/api/internals/metadata/message_content_test.h
index a2ef0cf8..dfce00f5 100644
--- a/src/tests/api/internals/metadata/message_content_test.h
+++ b/src/tests/api/internals/metadata/message_content_test.h
@@ -51,9 +51,14 @@ TEST(MessageContent, contentConstructorShouldStoreGivenStringAndLanguage) {
 
 TEST(MessageContent, contentShouldBeEqualIfStringsAreCaseInsensitivelyEqual) {
   MessageContent content1("content");
-  MessageContent content2("Content", french);
+  MessageContent content2("content", french);
 
   EXPECT_TRUE(content1 == content2);
+
+  content1 = MessageContent("content");
+  content2 = MessageContent("Content", french);
+
+  EXPECT_FALSE(content1 == content2);
 }
 
 TEST(MessageContent,
@@ -65,13 +70,19 @@ TEST(MessageContent,
 }
 
 TEST(MessageContent,
-     LessThanOperatorShouldUseCaseInsensitiveLexicographicalComparison) {
+     lessThanOperatorShouldUseCaseSensitiveLexicographicalComparison) {
   MessageContent content1("content");
-  MessageContent content2("Content", french);
+  MessageContent content2("content", french);
 
   EXPECT_FALSE(content1 < content2);
   EXPECT_FALSE(content2 < content1);
 
+  content1 = MessageContent("content", french);
+  content2 = MessageContent("Content");
+
+  EXPECT_FALSE(content1 < content2);
+  EXPECT_TRUE(content2 < content1);
+
   content1 = MessageContent("content1", french);
   content2 = MessageContent("content2");
 
diff --git a/src/tests/api/internals/metadata/tag_test.h b/src/tests/api/internals/metadata/tag_test.h
index 3593ed73..97bd7570 100644
--- a/src/tests/api/internals/metadata/tag_test.h
+++ b/src/tests/api/internals/metadata/tag_test.h
@@ -52,10 +52,15 @@ TEST(Tag, dataConstructorShouldSetFieldsToGivenValues) {
 
 TEST(Tag,
      tagsWithCaseInsensitiveEqualNamesAndEqualAdditionStatesShouldBeEqual) {
-  Tag tag1("Name", true, "condition1");
+  Tag tag1("name", true, "condition1");
   Tag tag2("name", true, "condition2");
 
   EXPECT_TRUE(tag1 == tag2);
+
+  tag1 = Tag("name");
+  tag2 = Tag("Name");
+
+  EXPECT_FALSE(tag1 == tag2);
 }
 
 TEST(Tags, tagsWithUnequalNamesShouldNotBeEqual) {
@@ -74,13 +79,19 @@ TEST(Tag, tagsWithUnequalAdditionStatesShouldNotBeEqual) {
 
 TEST(
     Tag,
-    lessThanOperatorShouldCaseInsensitivelyLexicographicallyCompareNameStrings) {
-  Tag tag1("Name");
+    lessThanOperatorShouldCaseSensitivelyLexicographicallyCompareNameStrings) {
+  Tag tag1("name");
   Tag tag2("name");
 
   EXPECT_FALSE(tag1 < tag2);
   EXPECT_FALSE(tag2 < tag1);
 
+  tag1 = Tag("name");
+  tag2 = Tag("Name");
+
+  EXPECT_FALSE(tag1 < tag2);
+  EXPECT_TRUE(tag2 < tag1);
+
   tag1 = Tag("name1");
   tag2 = Tag("name2");