diff --git a/lib/nanoc/base/entities/props.rb b/lib/nanoc/base/entities/props.rb
index 1bf6c5de09..8436d20bc5 100644
--- a/lib/nanoc/base/entities/props.rb
+++ b/lib/nanoc/base/entities/props.rb
@@ -9,7 +9,7 @@ class Props
     attr_reader :raw_content
 
     # TODO: Split raw_content for documents and collections
-    C_RAW_CONTENT = C::Or[C::IterOf[String], C::Bool]
+    C_RAW_CONTENT = C::Or[C::IterOf[C::Or[String, Regexp]], C::Bool]
     C_ATTRS = C::Or[C::IterOf[Symbol], C::Bool]
     contract C::KeywordArgs[raw_content: C::Optional[C_RAW_CONTENT], attributes: C::Optional[C_ATTRS], compiled_content: C::Optional[C::Bool], path: C::Optional[C::Bool]] => C::Any
     def initialize(raw_content: false, attributes: false, compiled_content: false, path: false)
diff --git a/lib/nanoc/base/repos/dependency_store.rb b/lib/nanoc/base/repos/dependency_store.rb
index 9f2e5c064b..f17256437a 100644
--- a/lib/nanoc/base/repos/dependency_store.rb
+++ b/lib/nanoc/base/repos/dependency_store.rb
@@ -88,7 +88,7 @@ def objects_causing_outdatedness_of(object)
       refs2objs(@graph.direct_predecessors_of(obj2ref(object)))
     end
 
-    C_RAW_CONTENT = C::Or[C::IterOf[String], C::Bool]
+    C_RAW_CONTENT = C::Or[C::IterOf[C::Or[String, Regexp]], C::Bool]
     C_ATTR = C::Or[C::IterOf[Symbol], C::Bool]
     C_KEYWORD_PROPS = C::KeywordArgs[raw_content: C::Optional[C_RAW_CONTENT], attributes: C::Optional[C_ATTR], compiled_content: C::Optional[C::Bool], path: C::Optional[C::Bool]]
 
diff --git a/lib/nanoc/base/services/dependency_tracker.rb b/lib/nanoc/base/services/dependency_tracker.rb
index d4375039e0..4844354ac1 100644
--- a/lib/nanoc/base/services/dependency_tracker.rb
+++ b/lib/nanoc/base/services/dependency_tracker.rb
@@ -6,7 +6,7 @@ class DependencyTracker
     include Nanoc::Int::ContractsSupport
 
     C_OBJ = C::Or[Nanoc::Int::Item, Nanoc::Int::Layout, Nanoc::Int::Configuration, Nanoc::Int::IdentifiableCollection]
-    C_RAW_CONTENT = C::Or[C::IterOf[String], C::Bool]
+    C_RAW_CONTENT = C::Or[C::IterOf[C::Or[String, Regexp]], C::Bool]
     C_ATTR = C::Or[C::IterOf[Symbol], C::Bool]
     C_ARGS = C::KeywordArgs[raw_content: C::Optional[C_RAW_CONTENT], attributes: C::Optional[C_ATTR], compiled_content: C::Optional[C::Bool], path: C::Optional[C::Bool]]
 
diff --git a/lib/nanoc/base/views/identifiable_collection_view.rb b/lib/nanoc/base/views/identifiable_collection_view.rb
index 7ec6e50b5b..d2adadce39 100644
--- a/lib/nanoc/base/views/identifiable_collection_view.rb
+++ b/lib/nanoc/base/views/identifiable_collection_view.rb
@@ -47,13 +47,12 @@ def size
     #
     # @return [Enumerable]
     def find_all(arg)
-      # TODO: support regex
       prop_attribute =
         case arg
-        when String
-          [arg]
-        when Nanoc::Identifier
+        when String, Nanoc::Identifier
           [arg.to_s]
+        when Regexp
+          [arg]
         else
           true
         end
@@ -85,13 +84,12 @@ def find_all(arg)
     #
     #   @return [#identifier] if an object was found
     def [](arg)
-      # TODO: support regex
       prop_attribute =
         case arg
-        when String
-          [arg]
-        when Nanoc::Identifier
+        when String, Nanoc::Identifier
           [arg.to_s]
+        when Regexp
+          [arg]
         else
           true
         end
diff --git a/spec/nanoc/base/services/outdatedness_checker_spec.rb b/spec/nanoc/base/services/outdatedness_checker_spec.rb
index 51a29d05d3..c7a8e06dde 100644
--- a/spec/nanoc/base/services/outdatedness_checker_spec.rb
+++ b/spec/nanoc/base/services/outdatedness_checker_spec.rb
@@ -572,7 +572,7 @@
         end
       end
 
-      context 'dependency on specific new items' do
+      context 'dependency on specific new items (string)' do
         before do
           dependency_tracker = Nanoc::Int::DependencyTracker.new(dependency_store)
           dependency_tracker.enter(item)
@@ -613,6 +613,48 @@
           it { is_expected.not_to be }
         end
       end
+
+      context 'dependency on specific new items (regex)' do
+        before do
+          dependency_tracker = Nanoc::Int::DependencyTracker.new(dependency_store)
+          dependency_tracker.enter(item)
+          dependency_tracker.bounce(items, raw_content: [%r{^/new.*}])
+          dependency_store.store
+        end
+
+        context 'nothing changed' do
+          it { is_expected.not_to be }
+        end
+
+        context 'matching item added' do
+          before do
+            new_item = Nanoc::Int::Item.new('stuff', {}, '/newblahz.md')
+            dependency_store.items = Nanoc::Int::ItemCollection.new(config, items.to_a + [new_item])
+            dependency_store.load
+          end
+
+          it { is_expected.to be }
+        end
+
+        context 'non-matching item added' do
+          before do
+            new_item = Nanoc::Int::Item.new('stuff', {}, '/nublahz.md')
+            dependency_store.items = Nanoc::Int::ItemCollection.new(config, items.to_a + [new_item])
+            dependency_store.load
+          end
+
+          it { is_expected.not_to be }
+        end
+
+        context 'item removed' do
+          before do
+            dependency_store.items = Nanoc::Int::ItemCollection.new(config, [])
+            dependency_store.load
+          end
+
+          it { is_expected.not_to be }
+        end
+      end
     end
 
     context 'only layout collection dependency' do
diff --git a/spec/nanoc/base/views/identifiable_collection_view_spec.rb b/spec/nanoc/base/views/identifiable_collection_view_spec.rb
index bec39d1cb4..2483037ddc 100644
--- a/spec/nanoc/base/views/identifiable_collection_view_spec.rb
+++ b/spec/nanoc/base/views/identifiable_collection_view_spec.rb
@@ -215,7 +215,7 @@
       let(:arg) { %r{\A/home} }
 
       it 'creates dependency' do
-        expect(dependency_tracker).to receive(:bounce).with(wrapped, raw_content: true)
+        expect(dependency_tracker).to receive(:bounce).with(wrapped, raw_content: [%r{\A/home}])
         subject
       end
 
@@ -261,7 +261,7 @@
       let(:arg) { %r{\.css\z} }
 
       it 'creates dependency' do
-        expect(dependency_tracker).to receive(:bounce).with(wrapped, raw_content: true)
+        expect(dependency_tracker).to receive(:bounce).with(wrapped, raw_content: [%r{\.css\z}])
         subject
       end