diff --git a/.instrumentation_generator/templates/gemspec.tt b/.instrumentation_generator/templates/gemspec.tt
index 7d5ee8de1..b9cc7e653 100644
--- a/.instrumentation_generator/templates/gemspec.tt
+++ b/.instrumentation_generator/templates/gemspec.tt
@@ -38,6 +38,8 @@ Gem::Specification.new do |spec|
   spec.add_development_dependency 'webmock', '~> 3.7.6'
   spec.add_development_dependency 'yard', '~> 0.9'
   spec.add_development_dependency 'yard-doctest', '~> 0.1.6'
+  # TODO Add semantic version constraints
+  spec.add_development_dependency '<%= instrumentation_name %>'
 
   if spec.respond_to?(:metadata)
     spec.metadata['changelog_uri'] = "https://open-telemetry.github.io/opentelemetry-ruby/opentelemetry-instrumentation-<%= instrumentation_name %>/v#{OpenTelemetry::Instrumentation::<%= pascal_cased_instrumentation_name %>::VERSION}/file.CHANGELOG.html"
diff --git a/.instrumentation_generator/templates/lib/instrumentation/instrumentation_name/instrumentation.rb.tt b/.instrumentation_generator/templates/lib/instrumentation/instrumentation_name/instrumentation.rb.tt
index 72c3ff815..e5cf596a8 100644
--- a/.instrumentation_generator/templates/lib/instrumentation/instrumentation_name/instrumentation.rb.tt
+++ b/.instrumentation_generator/templates/lib/instrumentation/instrumentation_name/instrumentation.rb.tt
@@ -9,6 +9,8 @@ module OpenTelemetry
     module <%= pascal_cased_instrumentation_name %>
       # The Instrumentation class contains logic to detect and install the <%= pascal_cased_instrumentation_name %> instrumentation
       class Instrumentation < OpenTelemetry::Instrumentation::Base
+        instrumented_library_name '<%= instrumentation_name %>'
+
         install do |_config|
           require_dependencies
         end
diff --git a/instrumentation/base/lib/opentelemetry/instrumentation/base.rb b/instrumentation/base/lib/opentelemetry/instrumentation/base.rb
index 582c96271..fb2c6a8ba 100644
--- a/instrumentation/base/lib/opentelemetry/instrumentation/base.rb
+++ b/instrumentation/base/lib/opentelemetry/instrumentation/base.rb
@@ -12,14 +12,15 @@ module Instrumentation
     # it with +OpenTelemetry.instrumentation_registry+ and make it available for
     # discovery and installation by an SDK.
     #
-    # A typical subclass of Base will provide an install block, a present
-    # block, and possibly a compatible block. Below is an
-    # example:
+    # A typical subclass of Base will provide a library name, an install block, a present block, e.g.:
     #
     # module OpenTelemetry
     #   module Instrumentation
     #     module Sinatra
     #       class Instrumentation < OpenTelemetry::Instrumentation::Base
+    #         # Declare instrumented library:
+    #         instrumented_library_name 'sinatra'
+    #
     #         install do |config|
     #           # install instrumentation, either by library hook or applying
     #           # a monkey patch
@@ -29,10 +30,32 @@ module Instrumentation
     #         present do
     #           defined?(::Sinatra)
     #         end
+    #       end
+    #     end
+    #   end
+    # end
+    #
+    # In cases where the instrumentation is not able to use `instrumented_library_name` to check against gem specifications,
+    # subclasses may provide a custom code block to check compatibility at start up time, e.g.
+    #
+    # module OpenTelemetry
+    #   module Instrumentation
+    #     module CustomLibrary
+    #       class Instrumentation < OpenTelemetry::Instrumentation::Base
+    #         MIN_VERSION = '3.2.1'
+    #         install do |config|
+    #           # install instrumentation, either by library hook or applying
+    #           # a monkey patch
+    #         end
+    #
+    #         # determine if the target library is present
+    #         present do
+    #           defined?(::CustomLibrary)
+    #         end
     #
     #         # if the target library is present, is it compatible?
     #         compatible do
-    #           Gem.loaded_specs['sinatra'].version > MIN_VERSION
+    #           ::CustomLibrary::VERSION > MIN_VERSION
     #         end
     #       end
     #     end
@@ -107,6 +130,14 @@ def instrumentation_version(instrumentation_version = nil)
           end
         end
 
+        # Optionally set the library name being instrumented.
+        #
+        # Set this value in lieu writing a custom compatible block.
+        # @param [String] instrumented_library_name must match the gem specification name of the instrumented library
+        def instrumented_library_name(instrumented_library_name = nil)
+          @instrumented_library_name ||= instrumented_library_name
+        end
+
         # The install block for this instrumentation. This will be where you install
         # instrumentation, either by framework hook or applying a monkey patch.
         #
@@ -163,7 +194,7 @@ def option(name, default:, validate:)
         end
 
         def instance
-          @instance ||= new(instrumentation_name, instrumentation_version, install_blk,
+          @instance ||= new(instrumentation_name, instrumentation_version, instrumented_library_name, install_blk,
                             present_blk, compatible_blk, options)
         end
 
@@ -189,11 +220,11 @@ def infer_version
         end
       end
 
-      attr_reader :name, :version, :config, :installed, :tracer
+      attr_reader :name, :version, :config, :installed, :tracer, :instrumented_library_name, :instrumentation_gem_name
 
       alias installed? installed
 
-      def initialize(name, version, install_blk, present_blk,
+      def initialize(name, version, instrumented_library_name, install_blk, present_blk,
                      compatible_blk, options)
         @name = name
         @version = version
@@ -204,6 +235,8 @@ def initialize(name, version, install_blk, present_blk,
         @installed = false
         @options = options
         @tracer = OpenTelemetry::Trace::Tracer.new
+        @instrumented_library_name = instrumented_library_name
+        @instrumentation_gem_name = @instrumented_library_name.nil? ? nil : "opentelemetry-instrumentation-#{@instrumented_library_name}"
       end
 
       # Install instrumentation with the given config. The present? and compatible?
@@ -238,12 +271,19 @@ def present?
         instance_exec(&@present_blk)
       end
 
-      # Calls the compatible block of the Instrumentation subclasses, if no block is provided
-      # it's assumed to be compatible
+      # Checks compatability of this instrumentation with its designated library
+      #
+      # Subclasses are compatible by default unless they specify
+      # - a custom compatible block
+      # - a `instrumented_library_name` use to compare gemspecs
       def compatible?
-        return true unless @compatible_blk
+        return true unless @compatible_blk || instrumented_library_name
 
-        instance_exec(&@compatible_blk)
+        if @compatible_blk
+          instance_exec(&@compatible_blk)
+        else
+          compatible_version?
+        end
       end
 
       # Whether this instrumentation is enabled. It first checks to see if it's enabled
@@ -260,6 +300,27 @@ def enabled?(config = nil)
 
       private
 
+      # EXPERIMENTAL: Checks compatability of `instrumented_library_name` against the `development_dependency` declared in instrumentations gemspec
+      #
+      # This method will first search `Gem.loaded_specs` to locate gemspecs that have already been required by RubyGems or Bundler.
+      # In the case the gems were not loaded, or do not use RubyGems/Bundler, it will fallback to searching for installed gems via `Gem::Specification.find_by_name`.
+      #
+      # Instrumentation authors are encouraged to implement a `present` block to ensure the constants are availble to use in monkey patches.
+      #
+      # See https://github.com/DataDog/dd-trace-rb/pull/1510
+      # rubocop:disable Metrics/AbcSize
+      def compatible_version?
+        instrumentation_spec = Gem.loaded_specs.fetch(instrumentation_gem_name) { Gem::Specification.find_by_name(instrumentation_gem_name) }
+        library_spec = Gem.loaded_specs.fetch(instrumented_library_name) { Gem::Specification.find_by_name(instrumented_library_name) }
+
+        dependency = instrumentation_spec.development_dependencies.find { |spec| spec.name == instrumented_library_name }
+        dependency&.requirement&.satisfied_by?(library_spec&.version) == true
+      rescue Gem::MissingSpecError => e
+        OpenTelemetry.handle_error(message: 'Instrumentation Compatibility Check Error', exception: e)
+        false
+      end
+      # rubocop:enable Metrics/AbcSize
+
       # The config_options method is responsible for validating that the user supplied
       # config hash is valid.
       # Unknown configuration keys are not included in the final config hash.
diff --git a/instrumentation/base/test/instrumentation/base_test.rb b/instrumentation/base/test/instrumentation/base_test.rb
index b853474df..8fa98b9c4 100644
--- a/instrumentation/base/test/instrumentation/base_test.rb
+++ b/instrumentation/base/test/instrumentation/base_test.rb
@@ -123,6 +123,133 @@ def initialize(*args)
         _(instance.compatible?).must_equal(true)
       end
     end
+
+    describe 'with a library name' do
+      let(:instrumentation) do
+        Class.new(OpenTelemetry::Instrumentation::Base) do
+          instrumentation_name 'OpenTelemetry::Instrumentation::Example::Instrumentation'
+          instrumentation_version '0.0.1'
+          instrumented_library_name 'example'
+        end
+      end
+
+      let(:instrumented_library_name) do
+        'example'
+      end
+
+      let(:library_gem_spec_version) do
+        '1.3.8.beta2'
+      end
+
+      let(:instrumentation_gem_name) do
+        "opentelemetry-instrumentation-#{instrumented_library_name}"
+      end
+
+      describe 'when comparing gemspecs' do
+        let(:library_gem_spec) do
+          Gem::Specification.new do |spec|
+            spec.name = instrumented_library_name
+            spec.version = library_gem_spec_version
+          end
+        end
+
+        let(:instrumentation_gem_spec) do
+          Gem::Specification.new do |spec|
+            spec.name = instrumentation_gem_name
+            spec.add_development_dependency instrumented_library_name, '~> 1.1', '< 1.3.9'
+          end
+        end
+
+        let(:loaded_specs) do
+          {
+            instrumentation_gem_name => instrumentation_gem_spec,
+            instrumented_library_name => library_gem_spec
+          }
+        end
+
+        describe 'when gems are activated' do
+          describe 'with compatible versions' do
+            it 'returns true' do
+              Gem.stub(:loaded_specs, loaded_specs) do
+                _(instrumentation.instance.compatible?).must_equal(true)
+              end
+            end
+          end
+
+          describe 'with incompatible versions' do
+            let(:library_gem_spec_version) do
+              '1.3.9'
+            end
+
+            it 'returns false' do
+              Gem.stub(:loaded_specs, loaded_specs) do
+                _(instrumentation.instance.compatible?).must_equal(false)
+              end
+            end
+          end
+        end
+
+        describe 'when gems were not activated (e.g. without using bundler)' do
+          describe 'with compatible versions' do
+            it 'returns true' do
+              Gem.stub(:loaded_specs, {}) do
+                Gem::Specification.stub(:find_by_name, ->(name) { loaded_specs[name] }) do
+                  _(instrumentation.instance.compatible?).must_equal(true)
+                end
+              end
+            end
+          end
+
+          describe 'with incompatible versions' do
+            let(:library_gem_spec_version) do
+              '1.3.9'
+            end
+
+            it 'returns false' do
+              Gem.stub(:loaded_specs, {}) do
+                Gem::Specification.stub(:find_by_name, ->(name) { loaded_specs[name] }) do
+                  _(instrumentation.instance.compatible?).must_equal(false)
+                end
+              end
+            end
+          end
+        end
+
+        describe 'when the library is not installed' do
+          let(:loaded_specs) do
+            { instrumentation_gem_name => instrumentation_gem_spec }
+          end
+
+          it 'returns false' do
+            Gem.stub(:loaded_specs, {}) do
+              gem_finder = lambda do |name|
+                raise Gem::MissingSpecError.new(name, name) unless loaded_specs[name]
+
+                loaded_specs[name]
+              end
+
+              Gem::Specification.stub(:find_by_name, gem_finder) do
+                _(instrumentation.instance.compatible?).must_equal(false)
+              end
+            end
+          end
+        end
+
+        describe 'when library is not declared as a development dependency' do
+          let(:instrumentation_gem_spec) do
+            Gem::Specification.new do |spec|
+              spec.name = instrumentation_gem_name
+            end
+          end
+
+          it 'returns false' do
+            Gem.stub(:loaded_specs, loaded_specs) do
+              _(instrumentation.instance.compatible?).must_equal(false)
+            end
+          end
+        end
+      end
+    end
   end
 
   describe '#install' do