diff --git a/cmd/dev_server/flags.go b/cmd/dev_server/flags.go
index 16b0edc6..01ba78d8 100644
--- a/cmd/dev_server/flags.go
+++ b/cmd/dev_server/flags.go
@@ -2,5 +2,6 @@ package dev_server
 
 const (
 	ContextFlag           = "context"
+	OverrideFlag          = "override"
 	SourceEnvironmentFlag = "source"
 )
diff --git a/cmd/dev_server/start_server.go b/cmd/dev_server/start_server.go
index 0f5d881b..f990cba6 100644
--- a/cmd/dev_server/start_server.go
+++ b/cmd/dev_server/start_server.go
@@ -2,6 +2,7 @@ package dev_server
 
 import (
 	"context"
+	"encoding/json"
 	"errors"
 	"log"
 	"os/exec"
@@ -10,10 +11,12 @@ import (
 	"github.com/spf13/cobra"
 	"github.com/spf13/viper"
 
+	"github.com/launchdarkly/go-sdk-common/v3/ldcontext"
 	"github.com/launchdarkly/ldcli/cmd/cliflags"
 	resourcescmd "github.com/launchdarkly/ldcli/cmd/resources"
 	"github.com/launchdarkly/ldcli/cmd/validators"
 	"github.com/launchdarkly/ldcli/internal/dev_server"
+	"github.com/launchdarkly/ldcli/internal/dev_server/model"
 )
 
 func NewStartServerCmd(client dev_server.Client) *cobra.Command {
@@ -28,17 +31,61 @@ func NewStartServerCmd(client dev_server.Client) *cobra.Command {
 
 	cmd.SetUsageTemplate(resourcescmd.SubcommandUsageTemplate())
 
+	cmd.Flags().String(cliflags.ProjectFlag, "", "The project key")
+	_ = viper.BindPFlag(cliflags.ProjectFlag, cmd.Flags().Lookup(cliflags.ProjectFlag))
+
+	cmd.Flags().String(SourceEnvironmentFlag, "", "environment to copy flag values from")
+	_ = viper.BindPFlag(SourceEnvironmentFlag, cmd.Flags().Lookup(SourceEnvironmentFlag))
+
+	cmd.Flags().String(ContextFlag, "", `Stringified JSON representation of your context object ex. {"kind": "multi", "user": { "email": "test@gmail.com", "username": "foo", "key": "bar"}`)
+	_ = viper.BindPFlag(ContextFlag, cmd.Flags().Lookup(ContextFlag))
+
+	cmd.Flags().String(OverrideFlag, "", `Stringified JSON representation of flag overrides ex. {"flagName": true, "stringFlagName": "test" }`)
+	_ = viper.BindPFlag(OverrideFlag, cmd.Flags().Lookup(OverrideFlag))
+
 	return cmd
 }
 
 func startServer(client dev_server.Client) func(*cobra.Command, []string) error {
 	return func(cmd *cobra.Command, args []string) error {
 		ctx := context.Background()
+
+		var initialSetting model.InitialProjectSettings
+
+		if viper.IsSet(cliflags.ProjectFlag) && viper.IsSet(SourceEnvironmentFlag) {
+
+			initialSetting = model.InitialProjectSettings{
+				Enabled:    true,
+				ProjectKey: viper.GetString(cliflags.ProjectFlag),
+				EnvKey:     viper.GetString(SourceEnvironmentFlag),
+			}
+			if viper.IsSet(ContextFlag) {
+				var c ldcontext.Context
+				contextString := viper.GetString(ContextFlag)
+				err := c.UnmarshalJSON([]byte(contextString))
+				if err != nil {
+					return err
+				}
+				initialSetting.Context = &c
+			}
+
+			if viper.IsSet(OverrideFlag) {
+				var override map[string]model.FlagValue
+				overrideString := viper.GetString(OverrideFlag)
+				err := json.Unmarshal([]byte(overrideString), &override)
+				if err != nil {
+					return err
+				}
+				initialSetting.Overrides = override
+			}
+		}
+
 		params := dev_server.ServerParams{
-			AccessToken:  viper.GetString(cliflags.AccessTokenFlag),
-			BaseURI:      viper.GetString(cliflags.BaseURIFlag),
-			DevStreamURI: viper.GetString(cliflags.DevStreamURIFlag),
-			Port:         viper.GetString(cliflags.PortFlag),
+			AccessToken:            viper.GetString(cliflags.AccessTokenFlag),
+			BaseURI:                viper.GetString(cliflags.BaseURIFlag),
+			DevStreamURI:           viper.GetString(cliflags.DevStreamURIFlag),
+			Port:                   viper.GetString(cliflags.PortFlag),
+			InitialProjectSettings: initialSetting,
 		}
 
 		client.RunServer(ctx, params)
diff --git a/internal/dev_server/adapters/context.go b/internal/dev_server/adapters/context.go
new file mode 100644
index 00000000..a0d59611
--- /dev/null
+++ b/internal/dev_server/adapters/context.go
@@ -0,0 +1,12 @@
+package adapters
+
+import (
+	"context"
+	ldapi "github.com/launchdarkly/api-client-go/v14"
+)
+
+func WithApiAndSdk(ctx context.Context, client ldapi.APIClient, streamingUrl string) context.Context {
+	ctx = WithSdk(ctx, newSdk(streamingUrl))
+	ctx = WithApi(ctx, NewApi(client))
+	return ctx
+}
diff --git a/internal/dev_server/adapters/middleware.go b/internal/dev_server/adapters/middleware.go
index 3f2d0a07..f1a66064 100644
--- a/internal/dev_server/adapters/middleware.go
+++ b/internal/dev_server/adapters/middleware.go
@@ -13,8 +13,7 @@ func Middleware(client ldapi.APIClient, streamingUrl string) func(handler http.H
 	return func(handler http.Handler) http.Handler {
 		return http.HandlerFunc(func(writer http.ResponseWriter, request *http.Request) {
 			ctx := request.Context()
-			ctx = WithSdk(ctx, newSdk(streamingUrl))
-			ctx = WithApi(ctx, NewApi(client))
+			ctx = WithApiAndSdk(ctx, client, streamingUrl)
 			request = request.WithContext(ctx)
 			handler.ServeHTTP(writer, request)
 		})
diff --git a/internal/dev_server/dev_server.go b/internal/dev_server/dev_server.go
index 7166ec57..0e8712dd 100644
--- a/internal/dev_server/dev_server.go
+++ b/internal/dev_server/dev_server.go
@@ -25,10 +25,11 @@ type Client interface {
 }
 
 type ServerParams struct {
-	AccessToken  string
-	BaseURI      string
-	DevStreamURI string
-	Port         string
+	AccessToken            string
+	BaseURI                string
+	DevStreamURI           string
+	Port                   string
+	InitialProjectSettings model.InitialProjectSettings
 }
 
 type LDClient struct {
@@ -49,6 +50,7 @@ func (c LDClient) RunServer(ctx context.Context, serverParams ServerParams) {
 	if err != nil {
 		log.Fatal(err)
 	}
+	observers := model.NewObservers()
 	ss := api.NewStrictServer()
 	apiServer := api.NewStrictHandlerWithOptions(ss, nil, api.StrictHTTPServerOptions{
 		RequestErrorHandlerFunc:  api.RequestErrorHandler,
@@ -57,7 +59,7 @@ func (c LDClient) RunServer(ctx context.Context, serverParams ServerParams) {
 	r := mux.NewRouter()
 	r.Use(adapters.Middleware(*ldClient, serverParams.DevStreamURI))
 	r.Use(model.StoreMiddleware(sqlStore))
-	r.Use(model.ObserversMiddleware(model.NewObservers()))
+	r.Use(model.ObserversMiddleware(observers))
 	r.Handle("/", http.RedirectHandler("/ui/", http.StatusFound))
 	r.Handle("/ui", http.RedirectHandler("/ui/", http.StatusMovedPermanently))
 	r.PathPrefix("/ui/").Handler(http.StripPrefix("/ui/", ui.AssetHandler))
@@ -66,9 +68,18 @@ func (c LDClient) RunServer(ctx context.Context, serverParams ServerParams) {
 	handler = handlers.CombinedLoggingHandler(os.Stdout, handler)
 	handler = handlers.RecoveryHandler(handlers.PrintRecoveryStack(true))(handler)
 
+	ctx = adapters.WithApiAndSdk(ctx, *ldClient, serverParams.DevStreamURI)
+	ctx = model.SetObserversOnContext(ctx, observers)
+	ctx = model.ContextWithStore(ctx, sqlStore)
+	syncErr := model.CreateOrSyncProject(ctx, serverParams.InitialProjectSettings)
+	if syncErr != nil {
+		log.Fatal(syncErr)
+	}
+
 	addr := fmt.Sprintf("0.0.0.0:%s", serverParams.Port)
 	log.Printf("Server running on %s", addr)
 	log.Printf("Access the UI for toggling overrides at http://localhost:%s/ui or by running `ldcli dev-server ui`", serverParams.Port)
+
 	server := http.Server{
 		Addr:    addr,
 		Handler: handler,
diff --git a/internal/dev_server/model/sync.go b/internal/dev_server/model/sync.go
new file mode 100644
index 00000000..dd0f323a
--- /dev/null
+++ b/internal/dev_server/model/sync.go
@@ -0,0 +1,53 @@
+package model
+
+import (
+	"context"
+	"log"
+
+	"github.com/pkg/errors"
+
+	"github.com/launchdarkly/go-sdk-common/v3/ldcontext"
+	"github.com/launchdarkly/go-sdk-common/v3/ldvalue"
+)
+
+type FlagValue = ldvalue.Value
+
+type InitialProjectSettings struct {
+	Enabled    bool
+	ProjectKey string
+	EnvKey     string
+	Context    *ldcontext.Context   `json:"context,omitempty"`
+	Overrides  map[string]FlagValue `json:"overrides,omitempty"`
+}
+
+func CreateOrSyncProject(ctx context.Context, settings InitialProjectSettings) error {
+	if !settings.Enabled {
+		return nil
+	}
+
+	log.Printf("Initial project [%s] with env [%s]", settings.ProjectKey, settings.EnvKey)
+	var project Project
+	project, createError := CreateProject(ctx, settings.ProjectKey, settings.EnvKey, settings.Context)
+	if createError != nil {
+		if errors.Is(createError, ErrAlreadyExists) {
+			log.Printf("Project [%s] exists, refreshing data", settings.ProjectKey)
+			var updateErr error
+			project, updateErr = UpdateProject(ctx, settings.ProjectKey, settings.Context, &settings.EnvKey)
+			if updateErr != nil {
+				return updateErr
+			}
+
+		} else {
+			return createError
+		}
+	}
+	for flagKey, val := range settings.Overrides {
+		_, err := UpsertOverride(ctx, settings.ProjectKey, flagKey, val)
+		if err != nil {
+			return err
+		}
+	}
+
+	log.Printf("Successfully synced Initial project [%s]", project.Key)
+	return nil
+}
diff --git a/internal/dev_server/model/sync_test.go b/internal/dev_server/model/sync_test.go
new file mode 100644
index 00000000..68c49f44
--- /dev/null
+++ b/internal/dev_server/model/sync_test.go
@@ -0,0 +1,173 @@
+package model_test
+
+import (
+	"context"
+	"testing"
+
+	"github.com/pkg/errors"
+	"github.com/stretchr/testify/assert"
+	"go.uber.org/mock/gomock"
+
+	ldapi "github.com/launchdarkly/api-client-go/v14"
+	"github.com/launchdarkly/go-sdk-common/v3/ldcontext"
+	"github.com/launchdarkly/go-sdk-common/v3/ldvalue"
+	"github.com/launchdarkly/go-server-sdk/v7/interfaces/flagstate"
+	adapters_mocks "github.com/launchdarkly/ldcli/internal/dev_server/adapters/mocks"
+	"github.com/launchdarkly/ldcli/internal/dev_server/model"
+	"github.com/launchdarkly/ldcli/internal/dev_server/model/mocks"
+)
+
+func TestInitialSync(t *testing.T) {
+
+	ctx := context.Background()
+	mockController := gomock.NewController(t)
+	observers := model.NewObservers()
+	ctx, api, sdk := adapters_mocks.WithMockApiAndSdk(ctx, mockController)
+	store := mocks.NewMockStore(mockController)
+	ctx = model.ContextWithStore(ctx, store)
+	ctx = model.SetObserversOnContext(ctx, observers)
+	projKey := "proj"
+	sourceEnvKey := "env"
+	sdkKey := "thing"
+
+	allFlagsState := flagstate.NewAllFlagsBuilder().
+		AddFlag("boolFlag", flagstate.FlagState{Value: ldvalue.Bool(true)}).
+		Build()
+
+	trueVariationId, falseVariationId := "true", "false"
+	allFlags := []ldapi.FeatureFlag{{
+		Name: "bool flag",
+		Kind: "bool",
+		Key:  "boolFlag",
+		Variations: []ldapi.Variation{
+			{
+				Id:    &trueVariationId,
+				Value: true,
+			},
+			{
+				Id:    &falseVariationId,
+				Value: false,
+			},
+		},
+	}}
+
+	t.Run("Returns no error if disabled", func(t *testing.T) {
+		input := model.InitialProjectSettings{
+			Enabled:    false,
+			ProjectKey: projKey,
+			EnvKey:     sourceEnvKey,
+			Context:    nil,
+			Overrides:  nil,
+		}
+		err := model.CreateOrSyncProject(ctx, input)
+		assert.NoError(t, err)
+	})
+
+	t.Run("Returns error if it cant fetch flag state", func(t *testing.T) {
+		api.EXPECT().GetSdkKey(gomock.Any(), projKey, sourceEnvKey).Return("", errors.New("fetch flag state fails"))
+		input := model.InitialProjectSettings{
+			Enabled:    true,
+			ProjectKey: projKey,
+			EnvKey:     sourceEnvKey,
+			Context:    nil,
+			Overrides:  nil,
+		}
+		err := model.CreateOrSyncProject(ctx, input)
+		assert.NotNil(t, err)
+		assert.Equal(t, "fetch flag state fails", err.Error())
+	})
+
+	t.Run("Returns error if it can't fetch flags", func(t *testing.T) {
+		api.EXPECT().GetSdkKey(gomock.Any(), projKey, sourceEnvKey).Return(sdkKey, nil)
+		sdk.EXPECT().GetAllFlagsState(gomock.Any(), gomock.Any(), sdkKey).Return(allFlagsState, nil)
+		api.EXPECT().GetAllFlags(gomock.Any(), projKey).Return(nil, errors.New("fetch flags failed"))
+		input := model.InitialProjectSettings{
+			Enabled:    true,
+			ProjectKey: projKey,
+			EnvKey:     sourceEnvKey,
+			Context:    nil,
+			Overrides:  nil,
+		}
+		err := model.CreateOrSyncProject(ctx, input)
+		assert.NotNil(t, err)
+		assert.Equal(t, "fetch flags failed", err.Error())
+	})
+
+	t.Run("Returns error if it fails to insert the project", func(t *testing.T) {
+		api.EXPECT().GetSdkKey(gomock.Any(), projKey, sourceEnvKey).Return(sdkKey, nil)
+		sdk.EXPECT().GetAllFlagsState(gomock.Any(), gomock.Any(), sdkKey).Return(allFlagsState, nil)
+		api.EXPECT().GetAllFlags(gomock.Any(), projKey).Return(allFlags, nil)
+		store.EXPECT().InsertProject(gomock.Any(), gomock.Any()).Return(errors.New("insert fails"))
+
+		input := model.InitialProjectSettings{
+			Enabled:    true,
+			ProjectKey: projKey,
+			EnvKey:     sourceEnvKey,
+			Context:    nil,
+			Overrides:  nil,
+		}
+		err := model.CreateOrSyncProject(ctx, input)
+		assert.NotNil(t, err)
+		assert.Equal(t, "insert fails", err.Error())
+	})
+
+	t.Run("Successfully creates project", func(t *testing.T) {
+		api.EXPECT().GetSdkKey(gomock.Any(), projKey, sourceEnvKey).Return(sdkKey, nil)
+		sdk.EXPECT().GetAllFlagsState(gomock.Any(), gomock.Any(), sdkKey).Return(allFlagsState, nil)
+		api.EXPECT().GetAllFlags(gomock.Any(), projKey).Return(allFlags, nil)
+		store.EXPECT().InsertProject(gomock.Any(), gomock.Any()).Return(nil)
+
+		input := model.InitialProjectSettings{
+			Enabled:    true,
+			ProjectKey: projKey,
+			EnvKey:     sourceEnvKey,
+			Context:    nil,
+			Overrides:  nil,
+		}
+		err := model.CreateOrSyncProject(ctx, input)
+
+		assert.NoError(t, err)
+	})
+	t.Run("Successfully creates project with override", func(t *testing.T) {
+		override := model.Override{
+			ProjectKey: projKey,
+			FlagKey:    "boolFlag",
+			Value:      ldvalue.Bool(true),
+			Active:     true,
+			Version:    1,
+		}
+
+		proj := model.Project{
+			Key:                  projKey,
+			SourceEnvironmentKey: sourceEnvKey,
+			Context:              ldcontext.New(t.Name()),
+			AllFlagsState: map[string]model.FlagState{
+				"boolFlag": {
+					Version: 0,
+					Value:   ldvalue.Bool(false),
+				},
+			},
+		}
+
+		api.EXPECT().GetSdkKey(gomock.Any(), projKey, sourceEnvKey).Return(sdkKey, nil)
+		sdk.EXPECT().GetAllFlagsState(gomock.Any(), gomock.Any(), sdkKey).Return(allFlagsState, nil)
+		api.EXPECT().GetAllFlags(gomock.Any(), projKey).Return(allFlags, nil)
+		store.EXPECT().InsertProject(gomock.Any(), gomock.Any()).Return(nil)
+		store.EXPECT().UpsertOverride(gomock.Any(), override).Return(override, nil)
+		store.EXPECT().GetDevProject(gomock.Any(), projKey).Return(&proj, nil)
+
+		input := model.InitialProjectSettings{
+			Enabled:    true,
+			ProjectKey: projKey,
+			EnvKey:     sourceEnvKey,
+			Context:    nil,
+			Overrides: map[string]model.FlagValue{
+				"boolFlag": ldvalue.Bool(true),
+			},
+		}
+		err := model.CreateOrSyncProject(ctx, input)
+
+		assert.NoError(t, err)
+	})
+
+}