diff --git a/.release-please-manifest.json b/.release-please-manifest.json
index 7f3ab495..56b4dffb 100644
--- a/.release-please-manifest.json
+++ b/.release-please-manifest.json
@@ -1,3 +1,3 @@
 {
-  ".": "8.4.2"
+  ".": "8.5.0"
 }
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 448158b3..c396af08 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,19 @@
 
 All notable changes to the LaunchDarkly Ruby SDK will be documented in this file. This project adheres to [Semantic Versioning](http://semver.org).
 
+## [8.5.0](https://github.com/launchdarkly/ruby-server-sdk/compare/8.4.2...8.5.0) (2024-06-10)
+
+
+### Features
+
+* Support to_h and to_json methods for LDContext ([#284](https://github.com/launchdarkly/ruby-server-sdk/issues/284)) ([d3c8d40](https://github.com/launchdarkly/ruby-server-sdk/commit/d3c8d409b631f559239e48fb93eb5e4f9181254f))
+
+
+### Bug Fixes
+
+* Increment flag & segment versions when reloading from file data source ([#285](https://github.com/launchdarkly/ruby-server-sdk/issues/285)) ([7d5b051](https://github.com/launchdarkly/ruby-server-sdk/commit/7d5b051ec1b1e8990a7fb3def5798f064acd5e04))
+* Log warning if client init timeout is considered high ([#278](https://github.com/launchdarkly/ruby-server-sdk/issues/278)) ([61f4c7e](https://github.com/launchdarkly/ruby-server-sdk/commit/61f4c7e589e9d0da94e4f289e9c601aa36028c95))
+
 ## [8.4.2](https://github.com/launchdarkly/ruby-server-sdk/compare/8.4.1...8.4.2) (2024-05-03)
 
 
diff --git a/PROVENANCE.md b/PROVENANCE.md
index 4cc73457..a597331d 100644
--- a/PROVENANCE.md
+++ b/PROVENANCE.md
@@ -9,7 +9,7 @@ To verify SLSA provenance attestations, we recommend using [slsa-verifier](https
 <!-- x-release-please-start-version -->
 ```
 # Set the version of the SDK to verify
-SDK_VERSION=8.4.2
+SDK_VERSION=8.5.0
 ```
 <!-- x-release-please-end -->
 
diff --git a/lib/ldclient-rb/context.rb b/lib/ldclient-rb/context.rb
index 9c331a3a..c9dd4618 100644
--- a/lib/ldclient-rb/context.rb
+++ b/lib/ldclient-rb/context.rb
@@ -354,6 +354,49 @@ def [](key)
       multi_kind? ? individual_context(key.to_s) : get_value(key)
     end
 
+    #
+    # Convert the LDContext to a JSON string.
+    #
+    # @param args [Array]
+    # @return [String]
+    #
+    def to_json(*args)
+      JSON.generate(to_h, *args)
+    end
+
+    #
+    # Convert the LDContext to a hash. If the LDContext is invalid, the hash will contain an error key with the error
+    # message.
+    #
+    # @return [Hash]
+    #
+    def to_h
+      return {error: error} unless valid?
+      return hash_single_kind unless multi_kind?
+
+      hash = {kind: 'multi'}
+      @contexts.each do |context|
+        single_kind_hash = context.to_h
+        kind = single_kind_hash.delete(:kind)
+        hash[kind] = single_kind_hash
+      end
+
+      hash
+    end
+
+    protected def hash_single_kind
+      hash = attributes.nil? ? {} : attributes.clone
+
+      hash[:kind] = kind
+      hash[:key] = key
+
+      hash[:name] = name unless name.nil?
+      hash[:anonymous] = anonymous if anonymous
+      hash[:_meta] = {privateAttributes: private_attributes} unless private_attributes.empty?
+
+      hash
+    end
+
     #
     # Retrieve the value of any top level, addressable attribute.
     #
diff --git a/lib/ldclient-rb/impl/integrations/file_data_source.rb b/lib/ldclient-rb/impl/integrations/file_data_source.rb
index c5ee917f..1e7ad078 100644
--- a/lib/ldclient-rb/impl/integrations/file_data_source.rb
+++ b/lib/ldclient-rb/impl/integrations/file_data_source.rb
@@ -40,6 +40,9 @@ def initialize(data_store, data_source_update_sink, logger, options={})
           @poll_interval = options[:poll_interval] || 1
           @initialized = Concurrent::AtomicBoolean.new(false)
           @ready = Concurrent::Event.new
+
+          @version_lock = Mutex.new
+          @last_version = 1
         end
 
         def initialized?
@@ -93,14 +96,22 @@ def load_all
         end
 
         def load_file(path, all_data)
+          version = 1
+          @version_lock.synchronize {
+            version = @last_version
+            @last_version += 1
+          }
+
           parsed = parse_content(IO.read(path))
           (parsed[:flags] || {}).each do |key, flag|
+            flag[:version] = version
             add_item(all_data, FEATURES, flag)
           end
           (parsed[:flagValues] || {}).each do |key, value|
-            add_item(all_data, FEATURES, make_flag_with_value(key.to_s, value))
+            add_item(all_data, FEATURES, make_flag_with_value(key.to_s, value, version))
           end
           (parsed[:segments] || {}).each do |key, segment|
+            segment[:version] = version
             add_item(all_data, SEGMENTS, segment)
           end
         end
@@ -134,10 +145,11 @@ def add_item(all_data, kind, item)
           items[key] = Model.deserialize(kind, item)
         end
 
-        def make_flag_with_value(key, value)
+        def make_flag_with_value(key, value, version)
           {
             key: key,
             on: true,
+            version: version,
             fallthrough: { variation: 0 },
             variations: [ value ],
           }
diff --git a/lib/ldclient-rb/reference.rb b/lib/ldclient-rb/reference.rb
index d25ee06b..8c248fe3 100644
--- a/lib/ldclient-rb/reference.rb
+++ b/lib/ldclient-rb/reference.rb
@@ -238,6 +238,16 @@ def hash
       ([error] + components).hash
     end
 
+    #
+    # Convert the Reference to a JSON string.
+    #
+    # @param args [Array]
+    # @return [String]
+    #
+    def to_json(*args)
+      JSON.generate(@raw_path, *args)
+    end
+
     #
     # Performs unescaping of attribute reference path components:
     #
diff --git a/lib/ldclient-rb/version.rb b/lib/ldclient-rb/version.rb
index bb3e7898..cfe2e29d 100644
--- a/lib/ldclient-rb/version.rb
+++ b/lib/ldclient-rb/version.rb
@@ -1,3 +1,3 @@
 module LaunchDarkly
-  VERSION = "8.4.2" # x-release-please-version
+  VERSION = "8.5.0" # x-release-please-version
 end
diff --git a/spec/context_spec.rb b/spec/context_spec.rb
index be261515..44be8e4a 100644
--- a/spec/context_spec.rb
+++ b/spec/context_spec.rb
@@ -1,4 +1,5 @@
 require "ldclient-rb/context"
+require "json"
 
 module LaunchDarkly
   describe LDContext do
@@ -148,6 +149,64 @@ module LaunchDarkly
           expect(org_first.fully_qualified_key).to eq("org:b-org-key:user:a-user-key")
         end
       end
+
+      describe "converts back to JSON format" do
+        it "single kind contexts" do
+          contextHash = {
+            key: "launchdarkly",
+            kind: "org",
+            address: {
+              street: "1999 Harrison St Suite 1100",
+              city: "Oakland",
+              state: "CA",
+              zip: "94612",
+              _meta: {
+                privateAttributes: ["city"],
+              },
+            },
+          }
+          context = subject.create(contextHash)
+          contextJson = context.to_json
+          backToHash = JSON.parse(contextJson, symbolize_names: true)
+
+          expect(backToHash).to eq(contextHash)
+        end
+
+        it "multi kind contexts" do
+          contextHash = {
+            kind: "multi",
+            "org": {
+              key: "launchdarkly",
+              address: {
+                street: "1999 Harrison St Suite 1100",
+                city: "Oakland",
+                state: "CA",
+                zip: "94612",
+              },
+              _meta: {
+                privateAttributes: ["address/city"],
+              },
+            },
+            "user": {
+              key: "user-key",
+              name: "Ruby",
+              anonymous: true,
+            },
+          }
+          context = subject.create(contextHash)
+          contextJson = context.to_json
+          backToHash = JSON.parse(contextJson, symbolize_names: true)
+
+          expect(backToHash).to eq(contextHash)
+        end
+
+        it "invalid context returns error" do
+          context = subject.create({ key: "", kind: "user", name: "testing" })
+          expect(context.valid?).to be false
+          expect(context.to_h).to eq({ error: "context key must not be empty" })
+          expect(context.to_json).to eq({ error: "context key must not be empty" }.to_json)
+        end
+      end
     end
 
     describe "context counts" do