diff --git a/src-tauri/.sqlx/query-ca3485d87b060cd77c4114d2af544adf18f6f15341d9d5db40865e92a80da4e2.json b/src-tauri/.sqlx/query-05dca7fe15ab1bf03952e94498ef3130e16f752da72782783696eb2cca4736d5.json
similarity index 81%
rename from src-tauri/.sqlx/query-ca3485d87b060cd77c4114d2af544adf18f6f15341d9d5db40865e92a80da4e2.json
rename to src-tauri/.sqlx/query-05dca7fe15ab1bf03952e94498ef3130e16f752da72782783696eb2cca4736d5.json
index 118bdd64..bfe436e1 100644
--- a/src-tauri/.sqlx/query-ca3485d87b060cd77c4114d2af544adf18f6f15341d9d5db40865e92a80da4e2.json
+++ b/src-tauri/.sqlx/query-05dca7fe15ab1bf03952e94498ef3130e16f752da72782783696eb2cca4736d5.json
@@ -1,6 +1,6 @@
 {
   "db_name": "SQLite",
-  "query": "\n            SELECT\n                id, model, created_at, updated_at, theme, appearance,\n                theme_dark, theme_light, update_channel,\n                interface_font_size, interface_scale, editor_font_size, editor_soft_wrap\n            FROM settings\n            WHERE id = 'default'\n        ",
+  "query": "\n            SELECT\n                id, model, created_at, updated_at, theme, appearance,\n                theme_dark, theme_light, update_channel,\n                interface_font_size, interface_scale, editor_font_size, editor_soft_wrap, \n                open_workspace_new_window\n            FROM settings\n            WHERE id = 'default'\n        ",
   "describe": {
     "columns": [
       {
@@ -67,6 +67,11 @@
         "name": "editor_soft_wrap",
         "ordinal": 12,
         "type_info": "Bool"
+      },
+      {
+        "name": "open_workspace_new_window",
+        "ordinal": 13,
+        "type_info": "Bool"
       }
     ],
     "parameters": {
@@ -85,8 +90,9 @@
       false,
       false,
       false,
-      false
+      false,
+      true
     ]
   },
-  "hash": "ca3485d87b060cd77c4114d2af544adf18f6f15341d9d5db40865e92a80da4e2"
+  "hash": "05dca7fe15ab1bf03952e94498ef3130e16f752da72782783696eb2cca4736d5"
 }
diff --git a/src-tauri/.sqlx/query-efd8ba41ea909b18dd520c57c1d464c5ae057b720cbbedcaec1513d43535632c.json b/src-tauri/.sqlx/query-6b5edf45a6799cd7f87c23a3c7f818ad110d58c601f694a619d9345ae9e8e11d.json
similarity index 55%
rename from src-tauri/.sqlx/query-efd8ba41ea909b18dd520c57c1d464c5ae057b720cbbedcaec1513d43535632c.json
rename to src-tauri/.sqlx/query-6b5edf45a6799cd7f87c23a3c7f818ad110d58c601f694a619d9345ae9e8e11d.json
index eed32b7a..dcf32d4f 100644
--- a/src-tauri/.sqlx/query-efd8ba41ea909b18dd520c57c1d464c5ae057b720cbbedcaec1513d43535632c.json
+++ b/src-tauri/.sqlx/query-6b5edf45a6799cd7f87c23a3c7f818ad110d58c601f694a619d9345ae9e8e11d.json
@@ -1,12 +1,12 @@
 {
   "db_name": "SQLite",
-  "query": "\n            UPDATE settings SET (\n                theme, appearance, theme_dark, theme_light, update_channel,\n                interface_font_size, interface_scale, editor_font_size, editor_soft_wrap\n            ) = (?, ?, ?, ?, ?, ?, ?, ?, ?) WHERE id = 'default';\n        ",
+  "query": "\n            UPDATE settings SET (\n                theme, appearance, theme_dark, theme_light, update_channel,\n                interface_font_size, interface_scale, editor_font_size, editor_soft_wrap,\n                open_workspace_new_window\n            ) = (?, ?, ?, ?, ?, ?, ?, ?, ?, ?) WHERE id = 'default';\n        ",
   "describe": {
     "columns": [],
     "parameters": {
-      "Right": 9
+      "Right": 10
     },
     "nullable": []
   },
-  "hash": "efd8ba41ea909b18dd520c57c1d464c5ae057b720cbbedcaec1513d43535632c"
+  "hash": "6b5edf45a6799cd7f87c23a3c7f818ad110d58c601f694a619d9345ae9e8e11d"
 }
diff --git a/src-tauri/Cargo.toml b/src-tauri/Cargo.toml
index 1d3605b8..0a02e6e7 100644
--- a/src-tauri/Cargo.toml
+++ b/src-tauri/Cargo.toml
@@ -30,27 +30,27 @@ base64 = "0.22.0"
 boa_engine = { version = "0.18.0", features = ["annex-b"] }
 boa_runtime = { version = "0.18.0" }
 chrono = { version = "0.4.31", features = ["serde"] }
+datetime = "0.5.2"
+hex_color = "3.0.0"
 http = "0.2.10"
+log = "0.4.21"
 rand = "0.8.5"
+regex = "1.10.2"
 reqwest = { version = "0.11.23", features = ["multipart", "cookies", "gzip", "brotli", "deflate", "json"] }
+reqwest_cookie_store = "0.6.0"
 serde = { version = "1.0.198", features = ["derive"] }
 serde_json = { version = "1.0.116", features = ["raw_value"] }
 sqlx = { version = "0.7.4", features = ["sqlite", "runtime-tokio-rustls", "json", "chrono", "time"] }
 tauri = { version = "2.0.0-beta", features = ["config-toml", "devtools", "protocol-asset"] }
 tauri-plugin-clipboard-manager = "2.1.0-beta"
+tauri-plugin-deep-link = "2.0.0-beta"
 tauri-plugin-dialog = "2.0.0-beta"
+tauri-plugin-fs = "2.0.0-beta"
 tauri-plugin-log = { version = "2.0.0-beta", features = ["colored"] }
-tauri-plugin-shell = "2.0.0-beta"
 tauri-plugin-os = "2.0.0-beta"
+tauri-plugin-shell = "2.0.0-beta"
 tauri-plugin-updater = "2.0.0-beta"
 tauri-plugin-window-state = "2.0.0-beta"
-tauri-plugin-fs = "2.0.0-beta"
-tauri-plugin-deep-link = "2.0.0-beta"
 tokio = { version = "1.36.0", features = ["sync"] }
-uuid = "1.7.0"
-log = "0.4.21"
-datetime = "0.5.2"
-reqwest_cookie_store = "0.6.0"
 tokio-stream = "0.1.15"
-regex = "1.10.2"
-hex_color = "3.0.0"
+uuid = "1.7.0"
diff --git a/src-tauri/migrations/20240607151115_open-workspace-setting.sql b/src-tauri/migrations/20240607151115_open-workspace-setting.sql
new file mode 100644
index 00000000..99869d9c
--- /dev/null
+++ b/src-tauri/migrations/20240607151115_open-workspace-setting.sql
@@ -0,0 +1 @@
+ALTER TABLE settings ADD COLUMN open_workspace_new_window BOOLEAN NULL DEFAULT NULL;
diff --git a/src-tauri/src/models.rs b/src-tauri/src/models.rs
index 2982526f..82cca640 100644
--- a/src-tauri/src/models.rs
+++ b/src-tauri/src/models.rs
@@ -59,6 +59,7 @@ pub struct Settings {
     pub interface_scale: i64,
     pub editor_font_size: i64,
     pub editor_soft_wrap: bool,
+    pub open_workspace_new_window: Option<bool>,
 }
 
 #[derive(sqlx::FromRow, Debug, Clone, Serialize, Deserialize, Default)]
@@ -891,7 +892,8 @@ async fn get_settings(mgr: &impl Manager<Wry>) -> Result<Settings, sqlx::Error>
             SELECT
                 id, model, created_at, updated_at, theme, appearance,
                 theme_dark, theme_light, update_channel,
-                interface_font_size, interface_scale, editor_font_size, editor_soft_wrap
+                interface_font_size, interface_scale, editor_font_size, editor_soft_wrap, 
+                open_workspace_new_window
             FROM settings
             WHERE id = 'default'
         "#,
@@ -928,8 +930,9 @@ pub async fn update_settings(
         r#"
             UPDATE settings SET (
                 theme, appearance, theme_dark, theme_light, update_channel,
-                interface_font_size, interface_scale, editor_font_size, editor_soft_wrap
-            ) = (?, ?, ?, ?, ?, ?, ?, ?, ?) WHERE id = 'default';
+                interface_font_size, interface_scale, editor_font_size, editor_soft_wrap,
+                open_workspace_new_window
+            ) = (?, ?, ?, ?, ?, ?, ?, ?, ?, ?) WHERE id = 'default';
         "#,
         settings.theme,
         settings.appearance,
@@ -940,6 +943,7 @@ pub async fn update_settings(
         settings.interface_scale,
         settings.editor_font_size,
         settings.editor_soft_wrap,
+        settings.open_workspace_new_window,
     )
     .execute(&db)
     .await?;
diff --git a/src-web/components/OpenWorkspaceDialog.tsx b/src-web/components/OpenWorkspaceDialog.tsx
new file mode 100644
index 00000000..9222cf74
--- /dev/null
+++ b/src-web/components/OpenWorkspaceDialog.tsx
@@ -0,0 +1,64 @@
+import { useState } from 'react';
+import { useOpenWorkspace } from '../hooks/useOpenWorkspace';
+import { useSettings } from '../hooks/useSettings';
+import { useUpdateSettings } from '../hooks/useUpdateSettings';
+import type { Workspace } from '../lib/models';
+import { Button } from './core/Button';
+import { Checkbox } from './core/Checkbox';
+import { Icon } from './core/Icon';
+import { InlineCode } from './core/InlineCode';
+import { HStack, VStack } from './core/Stacks';
+
+interface Props {
+  hide: () => void;
+  workspace: Workspace;
+}
+
+export function OpenWorkspaceDialog({ hide, workspace }: Props) {
+  const openWorkspace = useOpenWorkspace();
+  const settings = useSettings();
+  const updateSettings = useUpdateSettings();
+  const [remember, setRemember] = useState<boolean>(false);
+
+  return (
+    <VStack space={3}>
+      <p>
+        Where would you like to open <InlineCode>{workspace.name}</InlineCode>?
+      </p>
+      <HStack space={2} justifyContent="start" className="flex-row-reverse">
+        <Button
+          className="focus"
+          color="primary"
+          onClick={() => {
+            hide();
+            openWorkspace.mutate({ workspace, inNewWindow: false });
+            if (remember) {
+              updateSettings.mutate({ openWorkspaceNewWindow: false });
+            }
+          }}
+        >
+          This Window
+        </Button>
+        <Button
+          className="focus"
+          color="secondary"
+          rightSlot={<Icon icon="externalLink" />}
+          onClick={() => {
+            hide();
+            openWorkspace.mutate({ workspace, inNewWindow: true });
+            if (remember) {
+              updateSettings.mutate({ openWorkspaceNewWindow: true });
+            }
+          }}
+        >
+          New Window
+        </Button>
+      </HStack>
+      {settings && (
+        <HStack justifyContent="end">
+          <Checkbox checked={remember} title="Remember my choice" onChange={setRemember} />
+        </HStack>
+      )}
+    </VStack>
+  );
+}
diff --git a/src-web/components/Settings/SettingsGeneral.tsx b/src-web/components/Settings/SettingsGeneral.tsx
index a793b83b..464073cd 100644
--- a/src-web/components/Settings/SettingsGeneral.tsx
+++ b/src-web/components/Settings/SettingsGeneral.tsx
@@ -50,6 +50,33 @@ export function SettingsGeneral() {
           onClick={() => checkForUpdates.mutateAsync()}
         />
       </div>
+      <Select
+        name="openWorkspace"
+        label="Open Workspace"
+        labelPosition="left"
+        size="sm"
+        value={
+          settings.openWorkspaceNewWindow === true
+            ? 'new'
+            : settings.openWorkspaceNewWindow === false
+            ? 'current'
+            : 'ask'
+        }
+        onChange={(v) => {
+          if (v === 'current') {
+            updateSettings.mutate({ openWorkspaceNewWindow: false });
+          } else if (v === 'new') {
+            updateSettings.mutate({ openWorkspaceNewWindow: true });
+          } else {
+            updateSettings.mutate({ openWorkspaceNewWindow: null });
+          }
+        }}
+        options={[
+          { label: 'Always Ask', value: 'ask' },
+          { label: 'Current Window', value: 'current' },
+          { label: 'New Window', value: 'new' },
+        ]}
+      />
       <Separator className="my-4" />
 
       <Heading size={2}>
diff --git a/src-web/components/WorkspaceActionsDropdown.tsx b/src-web/components/WorkspaceActionsDropdown.tsx
index d66ea86b..d6a00f79 100644
--- a/src-web/components/WorkspaceActionsDropdown.tsx
+++ b/src-web/components/WorkspaceActionsDropdown.tsx
@@ -1,13 +1,11 @@
-import { invoke } from '@tauri-apps/api/core';
 import classNames from 'classnames';
 import { memo, useMemo } from 'react';
 import { useActiveWorkspace } from '../hooks/useActiveWorkspace';
-import { useAppRoutes } from '../hooks/useAppRoutes';
 import { useCommand } from '../hooks/useCommands';
 import { useDeleteWorkspace } from '../hooks/useDeleteWorkspace';
+import { useOpenWorkspace } from '../hooks/useOpenWorkspace';
 import { usePrompt } from '../hooks/usePrompt';
-import { getRecentEnvironments } from '../hooks/useRecentEnvironments';
-import { getRecentRequests } from '../hooks/useRecentRequests';
+import { useSettings } from '../hooks/useSettings';
 import { useUpdateWorkspace } from '../hooks/useUpdateWorkspace';
 import { useWorkspaces } from '../hooks/useWorkspaces';
 import type { ButtonProps } from './core/Button';
@@ -16,8 +14,8 @@ import type { DropdownItem } from './core/Dropdown';
 import { Dropdown } from './core/Dropdown';
 import { Icon } from './core/Icon';
 import { InlineCode } from './core/InlineCode';
-import { HStack } from './core/Stacks';
 import { useDialog } from './DialogContext';
+import { OpenWorkspaceDialog } from './OpenWorkspaceDialog';
 
 type Props = Pick<ButtonProps, 'className' | 'justify' | 'forDropdown' | 'leftSlot'>;
 
@@ -33,7 +31,9 @@ export const WorkspaceActionsDropdown = memo(function WorkspaceActionsDropdown({
   const createWorkspace = useCommand('workspace.create');
   const dialog = useDialog();
   const prompt = usePrompt();
-  const routes = useAppRoutes();
+  const settings = useSettings();
+  const openWorkspace = useOpenWorkspace();
+  const openWorkspaceNewWindow = settings?.openWorkspaceNewWindow ?? null;
 
   const items: DropdownItem[] = useMemo(() => {
     const workspaceItems: DropdownItem[] = workspaces.map((w) => ({
@@ -41,58 +41,16 @@ export const WorkspaceActionsDropdown = memo(function WorkspaceActionsDropdown({
       label: w.name,
       leftSlot: w.id === activeWorkspaceId ? <Icon icon="check" /> : <Icon icon="empty" />,
       onSelect: async () => {
+        if (typeof openWorkspaceNewWindow === 'boolean') {
+          openWorkspace.mutate({ workspace: w, inNewWindow: openWorkspaceNewWindow });
+          return;
+        }
+
         dialog.show({
           id: 'open-workspace',
           size: 'sm',
           title: 'Open Workspace',
-          description: (
-            <>
-              Where would you like to open <InlineCode>{w.name}</InlineCode>?
-            </>
-          ),
-          render: ({ hide }) => {
-            return (
-              <HStack space={2} justifyContent="start" className="mt-4 mb-6 flex-row-reverse">
-                <Button
-                  className="focus"
-                  color="primary"
-                  onClick={async () => {
-                    hide();
-                    const environmentId = (await getRecentEnvironments(w.id))[0];
-                    const requestId = (await getRecentRequests(w.id))[0];
-                    if (requestId != null) {
-                      routes.navigate('request', { workspaceId: w.id, environmentId, requestId });
-                    } else {
-                      routes.navigate('workspace', { workspaceId: w.id, environmentId });
-                    }
-                  }}
-                >
-                  This Window
-                </Button>
-                <Button
-                  className="focus"
-                  color="secondary"
-                  rightSlot={<Icon icon="externalLink" />}
-                  onClick={async () => {
-                    hide();
-                    const environmentId = (await getRecentEnvironments(w.id))[0];
-                    const requestId = (await getRecentRequests(w.id))[0];
-                    const path =
-                      requestId != null
-                        ? routes.paths.request({
-                            workspaceId: w.id,
-                            environmentId,
-                            requestId,
-                          })
-                        : routes.paths.workspace({ workspaceId: w.id, environmentId });
-                    await invoke('cmd_new_window', { url: path });
-                  }}
-                >
-                  New Window
-                </Button>
-              </HStack>
-            );
-          },
+          render: ({ hide }) => <OpenWorkspaceDialog workspace={w} hide={hide} />,
         });
       },
     }));
@@ -152,8 +110,9 @@ export const WorkspaceActionsDropdown = memo(function WorkspaceActionsDropdown({
     createWorkspace,
     deleteWorkspace.mutate,
     dialog,
+    openWorkspace,
     prompt,
-    routes,
+    openWorkspaceNewWindow,
     updateWorkspace,
     workspaces,
   ]);
diff --git a/src-web/components/core/Dialog.tsx b/src-web/components/core/Dialog.tsx
index 66d74db3..5364aac6 100644
--- a/src-web/components/core/Dialog.tsx
+++ b/src-web/components/core/Dialog.tsx
@@ -67,7 +67,7 @@ export function Dialog({
               'rounded-lg',
               'border border-background-highlight-secondary shadow-lg shadow-[rgba(0,0,0,0.1)]',
               'max-w-[calc(100vw-5rem)] max-h-[calc(100vh-6rem)]',
-              size === 'sm' && 'w-[25rem] max-h-[80vh]',
+              size === 'sm' && 'w-[28rem] max-h-[80vh]',
               size === 'md' && 'w-[45rem] max-h-[80vh]',
               size === 'lg' && 'w-[65rem] max-h-[80vh]',
               size === 'full' && 'w-[100vw] h-[100vh]',
diff --git a/src-web/hooks/useOpenWorkspace.ts b/src-web/hooks/useOpenWorkspace.ts
new file mode 100644
index 00000000..e0f8c8b9
--- /dev/null
+++ b/src-web/hooks/useOpenWorkspace.ts
@@ -0,0 +1,50 @@
+import { useMutation } from '@tanstack/react-query';
+import { invoke } from '@tauri-apps/api/core';
+import type { Workspace } from '../lib/models';
+import { useAppRoutes } from './useAppRoutes';
+import { getRecentEnvironments } from './useRecentEnvironments';
+import { getRecentRequests } from './useRecentRequests';
+import { useSettings } from './useSettings';
+
+export function useOpenWorkspace() {
+  const settings = useSettings();
+  const routes = useAppRoutes();
+
+  return useMutation({
+    mutationFn: async ({
+      workspace,
+      inNewWindow,
+    }: {
+      workspace: Workspace;
+      inNewWindow: boolean;
+    }) => {
+      if (settings == null || workspace == null) return;
+
+      if (inNewWindow) {
+        const environmentId = (await getRecentEnvironments(workspace.id))[0];
+        const requestId = (await getRecentRequests(workspace.id))[0];
+        const path =
+          requestId != null
+            ? routes.paths.request({
+                workspaceId: workspace.id,
+                environmentId,
+                requestId,
+              })
+            : routes.paths.workspace({ workspaceId: workspace.id, environmentId });
+        await invoke('cmd_new_window', { url: path });
+      } else {
+        const environmentId = (await getRecentEnvironments(workspace.id))[0];
+        const requestId = (await getRecentRequests(workspace.id))[0];
+        if (requestId != null) {
+          routes.navigate('request', {
+            workspaceId: workspace.id,
+            environmentId,
+            requestId,
+          });
+        } else {
+          routes.navigate('workspace', { workspaceId: workspace.id, environmentId });
+        }
+      }
+    },
+  });
+}
diff --git a/src-web/lib/models.ts b/src-web/lib/models.ts
index c36d7c2b..c861e8f4 100644
--- a/src-web/lib/models.ts
+++ b/src-web/lib/models.ts
@@ -41,6 +41,7 @@ export interface Settings extends BaseModel {
   interfaceScale: number;
   editorFontSize: number;
   editorSoftWrap: boolean;
+  openWorkspaceNewWindow: boolean | null;
 }
 
 export interface Workspace extends BaseModel {