diff --git a/gui/src/app/App.tsx b/gui/src/app/App.tsx
index 6bea45a..98854d4 100644
--- a/gui/src/app/App.tsx
+++ b/gui/src/app/App.tsx
@@ -1,9 +1,9 @@
+import { CompileContextProvider } from "@SpCompilation/CompileContextProvider";
 import ToggleableThemeProvider from "./ToggleableThemeProvider";
 import ProjectContextProvider from "@SpCore/ProjectContextProvider";
 import HomePage from "@SpPages/HomePage";
 import { Analytics } from "@vercel/analytics/react";
 import { BrowserRouter } from "react-router-dom";
-import { CompileContextProvider } from "./CompileContext/CompileContextProvider";
 
 const App = () => {
   return (
diff --git a/gui/src/app/CompileContext/CompileContext.ts b/gui/src/app/Compilation/Context/CompileContext.ts
similarity index 86%
rename from gui/src/app/CompileContext/CompileContext.ts
rename to gui/src/app/Compilation/Context/CompileContext.ts
index cfd9d01..489ded2 100644
--- a/gui/src/app/CompileContext/CompileContext.ts
+++ b/gui/src/app/Compilation/Context/CompileContext.ts
@@ -16,6 +16,8 @@ type CompileContextType = {
   setValidSyntax: (valid: boolean) => void;
   stanWasmServerUrl: string;
   setStanWasmServerUrl: (url: string) => void;
+  isConnected: boolean;
+  retryConnection: () => void;
 };
 
 export const CompileContext = createContext<CompileContextType>({
@@ -26,4 +28,6 @@ export const CompileContext = createContext<CompileContextType>({
   setValidSyntax: () => {},
   stanWasmServerUrl: "",
   setStanWasmServerUrl: () => {},
+  isConnected: false,
+  retryConnection: () => {},
 });
diff --git a/gui/src/app/CompileContext/CompileContextProvider.tsx b/gui/src/app/Compilation/Context/CompileContextProvider.tsx
similarity index 68%
rename from gui/src/app/CompileContext/CompileContextProvider.tsx
rename to gui/src/app/Compilation/Context/CompileContextProvider.tsx
index 9ac5271..15a5ee8 100644
--- a/gui/src/app/CompileContext/CompileContextProvider.tsx
+++ b/gui/src/app/Compilation/Context/CompileContextProvider.tsx
@@ -1,5 +1,4 @@
 import { ProjectContext } from "@SpCore/ProjectContextProvider";
-import compileStanProgram from "@SpCompileContext/compileStanProgram";
 import {
   FunctionComponent,
   PropsWithChildren,
@@ -8,13 +7,42 @@ import {
   useEffect,
   useState,
 } from "react";
-import { CompileContext, CompileStatus } from "./CompileContext";
-import { publicCompilationServerUrl } from "@SpStanc/CompilationServerConnectionControl";
+import { CompileContext, CompileStatus } from "@SpCompilation/CompileContext";
+import { publicCompilationServerUrl } from "@SpCompilation/Constants";
+import compileStanProgram from "./compileStanProgram";
 
 type CompileContextProviderProps = {
   // none
 };
 
+const useIsConnected = (stanWasmServerUrl: string) => {
+  const probeUrl = `${stanWasmServerUrl}/probe`;
+  const [isConnected, setIsConnected] = useState<boolean>(false);
+  const [retryCode, setRetryCode] = useState<number>(0);
+  const retryConnection = useCallback(() => {
+    setRetryCode((r) => r + 1);
+  }, []);
+  useEffect(() => {
+    setIsConnected(false);
+    if (!probeUrl.startsWith("http://") && !probeUrl.startsWith("https://")) {
+      // important to do this check because otherwise fetch may succeed because
+      // the server of this web app may respond with success
+      return;
+    }
+    (async () => {
+      try {
+        const response = await fetch(probeUrl);
+        if (response.status === 200) {
+          setIsConnected(true);
+        }
+      } catch (err) {
+        setIsConnected(false);
+      }
+    })();
+  }, [probeUrl, retryCode]);
+  return { isConnected, retryConnection };
+};
+
 const initialStanWasmServerUrl =
   localStorage.getItem("stanWasmServerUrl") || publicCompilationServerUrl;
 
@@ -83,6 +111,8 @@ export const CompileContextProvider: FunctionComponent<
     stanWasmServerUrl,
   ]);
 
+  const { isConnected, retryConnection } = useIsConnected(stanWasmServerUrl);
+
   return (
     <CompileContext.Provider
       value={{
@@ -94,6 +124,8 @@ export const CompileContextProvider: FunctionComponent<
         setValidSyntax,
         stanWasmServerUrl,
         setStanWasmServerUrl,
+        isConnected,
+        retryConnection,
       }}
     >
       {children}
diff --git a/gui/src/app/CompileContext/compileStanProgram.ts b/gui/src/app/Compilation/Context/compileStanProgram.ts
similarity index 100%
rename from gui/src/app/CompileContext/compileStanProgram.ts
rename to gui/src/app/Compilation/Context/compileStanProgram.ts
diff --git a/gui/src/app/CompileContext/mainJsUrlCache.ts b/gui/src/app/Compilation/Context/mainJsUrlCache.ts
similarity index 100%
rename from gui/src/app/CompileContext/mainJsUrlCache.ts
rename to gui/src/app/Compilation/Context/mainJsUrlCache.ts
diff --git a/gui/src/app/CompilationServerConnectionControl/ConfigureCompilationServerDialog.tsx b/gui/src/app/Compilation/Control/CompilationServerDialog.tsx
similarity index 96%
rename from gui/src/app/CompilationServerConnectionControl/ConfigureCompilationServerDialog.tsx
rename to gui/src/app/Compilation/Control/CompilationServerDialog.tsx
index d6a179e..a955f1b 100644
--- a/gui/src/app/CompilationServerConnectionControl/ConfigureCompilationServerDialog.tsx
+++ b/gui/src/app/Compilation/Control/CompilationServerDialog.tsx
@@ -1,4 +1,4 @@
-import { CompileContext } from "@SpCompileContext/CompileContext";
+import { CompileContext } from "@SpCompilation/CompileContext";
 import { Refresh } from "@mui/icons-material";
 import Divider from "@mui/material/Divider";
 import FormControl from "@mui/material/FormControl";
@@ -10,11 +10,11 @@ import RadioGroup from "@mui/material/RadioGroup";
 import TextField from "@mui/material/TextField";
 import Typography from "@mui/material/Typography";
 import { FunctionComponent, useCallback, useContext } from "react";
+import { serverTypeForUrl } from "./CompilationServerToolbar";
 import {
   localCompilationServerUrl,
   publicCompilationServerUrl,
-  serverTypeForUrl,
-} from "./CompilationServerConnectionControl";
+} from "./Constants";
 
 type ConfigureCompilationServerDialogProps = {
   isConnected: boolean;
diff --git a/gui/src/app/CompilationServerConnectionControl/CompilationServerConnectionControl.tsx b/gui/src/app/Compilation/Control/CompilationServerToolbar.tsx
similarity index 53%
rename from gui/src/app/CompilationServerConnectionControl/CompilationServerConnectionControl.tsx
rename to gui/src/app/Compilation/Control/CompilationServerToolbar.tsx
index bdc50b5..6d27113 100644
--- a/gui/src/app/CompilationServerConnectionControl/CompilationServerConnectionControl.tsx
+++ b/gui/src/app/Compilation/Control/CompilationServerToolbar.tsx
@@ -3,23 +3,16 @@ import { Cancel, Check } from "@mui/icons-material";
 import CloseableDialog, {
   useDialogControls,
 } from "@SpComponents/CloseableDialog";
-import {
-  FunctionComponent,
-  useCallback,
-  useContext,
-  useEffect,
-  useState,
-} from "react";
-import ConfigureCompilationServerDialog from "./ConfigureCompilationServerDialog";
+import { FunctionComponent, useCallback, useContext } from "react";
+import ConfigureCompilationServerDialog from "./CompilationServerDialog";
 import IconButton from "@mui/material/IconButton";
 import Typography from "@mui/material/Typography";
-import { CompileContext } from "@SpCompileContext/CompileContext";
-
-export const publicCompilationServerUrl =
-  "https://stan-wasm.flatironinstitute.org";
-export const localCompilationServerUrl = "http://localhost:8083";
-
-type ServerType = "public" | "local" | "custom";
+import { CompileContext } from "@SpCompilation/CompileContext";
+import {
+  ServerType,
+  publicCompilationServerUrl,
+  localCompilationServerUrl,
+} from "./Constants";
 
 type CompilationServerConnectionControlProps = {
   // none
@@ -28,8 +21,8 @@ type CompilationServerConnectionControlProps = {
 const CompilationServerConnectionControl: FunctionComponent<
   CompilationServerConnectionControlProps
 > = () => {
-  const { stanWasmServerUrl } = useContext(CompileContext);
-  const { isConnected, retryConnection } = useIsConnected(stanWasmServerUrl);
+  const { stanWasmServerUrl, isConnected, retryConnection } =
+    useContext(CompileContext);
 
   const {
     handleOpen: openDialog,
@@ -80,32 +73,4 @@ export const serverTypeForUrl = (url: string): ServerType => {
       : "custom";
 };
 
-const useIsConnected = (stanWasmServerUrl: string) => {
-  const probeUrl = `${stanWasmServerUrl}/probe`;
-  const [isConnected, setIsConnected] = useState<boolean>(false);
-  const [retryCode, setRetryCode] = useState<number>(0);
-  const retryConnection = useCallback(() => {
-    setRetryCode((r) => r + 1);
-  }, []);
-  useEffect(() => {
-    setIsConnected(false);
-    if (!probeUrl.startsWith("http://") && !probeUrl.startsWith("https://")) {
-      // important to do this check because otherwise fetch may succeed because
-      // the server of this web app may respond with success
-      return;
-    }
-    (async () => {
-      try {
-        const response = await fetch(probeUrl);
-        if (response.status === 200) {
-          setIsConnected(true);
-        }
-      } catch (err) {
-        setIsConnected(false);
-      }
-    })();
-  }, [probeUrl, retryCode]);
-  return { isConnected, retryConnection };
-};
-
 export default CompilationServerConnectionControl;
diff --git a/gui/src/app/Compilation/Control/Constants.ts b/gui/src/app/Compilation/Control/Constants.ts
new file mode 100644
index 0000000..678cb20
--- /dev/null
+++ b/gui/src/app/Compilation/Control/Constants.ts
@@ -0,0 +1,4 @@
+export const publicCompilationServerUrl =
+  "https://stan-wasm.flatironinstitute.org";
+export const localCompilationServerUrl = "http://localhost:8083";
+export type ServerType = "public" | "local" | "custom";
diff --git a/gui/src/app/FileEditor/StanFileEditor.tsx b/gui/src/app/FileEditor/StanFileEditor.tsx
index d8eeb30..1182f2f 100644
--- a/gui/src/app/FileEditor/StanFileEditor.tsx
+++ b/gui/src/app/FileEditor/StanFileEditor.tsx
@@ -5,7 +5,7 @@ import TextEditor from "@SpComponents/TextEditor";
 import { ToolbarItem } from "@SpComponents/ToolBar";
 import { stancErrorsToCodeMarkers } from "@SpStanc/Linting";
 import useStanc from "@SpStanc/useStanc";
-import { CompileContext } from "@SpCompileContext/CompileContext";
+import { CompileContext } from "@SpCompilation/CompileContext";
 import { FunctionComponent, useContext, useMemo, useState } from "react";
 
 type Props = {
@@ -32,7 +32,7 @@ const StanFileEditor: FunctionComponent<Props> = ({
     setEditedFileContent,
   );
 
-  const { compileStatus, compileMessage, compile, validSyntax } =
+  const { compileStatus, compileMessage, compile, validSyntax, isConnected } =
     useContext(CompileContext);
 
   const hasWarnings = useMemo(() => {
@@ -89,17 +89,15 @@ const StanFileEditor: FunctionComponent<Props> = ({
       });
     }
     if (editedFileContent && editedFileContent === fileContent) {
-      if (compileStatus !== "compiling") {
-        if (validSyntax) {
-          ret.push({
-            type: "button",
-            tooltip: "Compile Stan model",
-            label: "Compile",
-            icon: <Settings />,
-            onClick: compile,
-            color: "info.dark",
-          });
-        }
+      if (compileStatus !== "compiling" && validSyntax && isConnected) {
+        ret.push({
+          type: "button",
+          tooltip: "Compile Stan model",
+          label: "Compile",
+          icon: <Settings />,
+          onClick: compile,
+          color: "info.dark",
+        });
       }
       if (compileStatus !== "") {
         ret.push({
@@ -118,15 +116,16 @@ const StanFileEditor: FunctionComponent<Props> = ({
 
     return ret;
   }, [
+    validSyntax,
     editedFileContent,
+    hasWarnings,
+    readOnly,
     fileContent,
-    compile,
     requestFormat,
-    validSyntax,
     compileStatus,
+    isConnected,
+    compile,
     compileMessage,
-    readOnly,
-    hasWarnings,
   ]);
 
   const isCompiling = compileStatus === "compiling";
diff --git a/gui/src/app/RunPanel/RunPanel.tsx b/gui/src/app/RunPanel/RunPanel.tsx
index ce1ee76..442ae77 100644
--- a/gui/src/app/RunPanel/RunPanel.tsx
+++ b/gui/src/app/RunPanel/RunPanel.tsx
@@ -1,18 +1,15 @@
 /* eslint-disable @typescript-eslint/no-explicit-any */
-import { FunctionComponent, useCallback, useContext } from "react";
+import { FunctionComponent, useCallback, useContext, useMemo } from "react";
 
 import Button from "@mui/material/Button";
-import { CompileContext } from "@SpCompileContext/CompileContext";
+import { CompileContext } from "@SpCompilation/CompileContext";
 import { ProjectContext } from "@SpCore/ProjectContextProvider";
-import {
-  ProjectDataModel,
-  SamplingOpts,
-  modelHasUnsavedChanges,
-} from "@SpCore/ProjectDataModel";
+import { SamplingOpts, modelHasUnsavedChanges } from "@SpCore/ProjectDataModel";
 import StanSampler from "@SpStanSampler/StanSampler";
 import { StanRun } from "@SpStanSampler/useStanSampler";
 import CompiledRunPanel from "./CompiledRunPanel";
 import CircularProgress from "@mui/material/CircularProgress";
+import Tooltip from "@mui/material/Tooltip";
 
 type RunPanelProps = {
   sampler?: StanSampler;
@@ -41,23 +38,36 @@ const RunPanel: FunctionComponent<RunPanelProps> = ({
     sampler.cancel();
   }, [sampler]);
 
-  const { compile, compileStatus, validSyntax } = useContext(CompileContext);
+  const { compile, compileStatus, validSyntax, isConnected } =
+    useContext(CompileContext);
 
   const { data: projectData } = useContext(ProjectContext);
 
+  const tooltip = useMemo(() => {
+    if (!validSyntax) return "Syntax error";
+    if (!isConnected) return "Not connected to compilation server";
+    if (!projectData.stanFileContent.trim()) return "No model to compile";
+    if (modelHasUnsavedChanges(projectData)) return "Model has unsaved changes";
+    return "";
+  }, [isConnected, projectData, validSyntax]);
+
   if (!dataIsSaved) {
     return <div className="RunPanelPadded">Data not saved</div>;
   }
 
   const compileDiv = (
     <div>
-      <Button
-        variant="contained"
-        onClick={compile}
-        disabled={isCompileModelDisabled(projectData, validSyntax)}
-      >
-        compile model
-      </Button>
+      <Tooltip title={tooltip}>
+        <span>
+          <Button
+            variant="contained"
+            onClick={compile}
+            disabled={tooltip != ""}
+          >
+            compile model
+          </Button>
+        </span>
+      </Tooltip>
     </div>
   );
 
@@ -89,14 +99,4 @@ const RunPanel: FunctionComponent<RunPanelProps> = ({
   );
 };
 
-const isCompileModelDisabled = (
-  projectData: ProjectDataModel,
-  validSyntax: boolean,
-) => {
-  if (!validSyntax) return true;
-  if (!projectData.stanFileContent.trim()) return true;
-  if (modelHasUnsavedChanges(projectData)) return true;
-  return false;
-};
-
 export default RunPanel;
diff --git a/gui/src/app/Stanc/useStanc.ts b/gui/src/app/Stanc/useStanc.ts
index cd24191..12162cb 100644
--- a/gui/src/app/Stanc/useStanc.ts
+++ b/gui/src/app/Stanc/useStanc.ts
@@ -7,7 +7,7 @@ import { useCallback, useContext, useEffect, useMemo, useState } from "react";
 // https://vitejs.dev/guide/assets#importing-script-as-a-worker
 // https://vitejs.dev/guide/assets#importing-asset-as-url
 import stancWorkerURL from "@SpStanc/stancWorker?worker&url";
-import { CompileContext } from "@SpCompileContext/CompileContext";
+import { CompileContext } from "@SpCompilation/CompileContext";
 
 const useStanc = (
   modelName: string,
diff --git a/gui/src/app/pages/HomePage/SamplingWindow/SamplingWindow.tsx b/gui/src/app/pages/HomePage/SamplingWindow/SamplingWindow.tsx
index 78ed28b..b5aaa52 100644
--- a/gui/src/app/pages/HomePage/SamplingWindow/SamplingWindow.tsx
+++ b/gui/src/app/pages/HomePage/SamplingWindow/SamplingWindow.tsx
@@ -15,7 +15,7 @@ import {
 import AnalysisPyWindow from "@SpScripting/Analysis/AnalysisPyWindow";
 import useStanSampler, { StanRun } from "@SpStanSampler/useStanSampler";
 import AnalysisRWindow from "@SpScripting/Analysis/AnalysisRWindow";
-import { CompileContext } from "@SpCompileContext/CompileContext";
+import { CompileContext } from "@SpCompilation/CompileContext";
 
 type SamplingWindowProps = {
   // none
diff --git a/gui/src/app/pages/HomePage/TopBar.tsx b/gui/src/app/pages/HomePage/TopBar.tsx
index 6099667..821f666 100644
--- a/gui/src/app/pages/HomePage/TopBar.tsx
+++ b/gui/src/app/pages/HomePage/TopBar.tsx
@@ -1,4 +1,4 @@
-import CompilationServerConnectionControl from "@SpStanc/CompilationServerConnectionControl";
+import CompilationServerConnectionControl from "@SpCompilation/CompilationServerToolbar";
 import { Brightness7, DarkMode, Menu, QuestionMark } from "@mui/icons-material";
 import AppBar from "@mui/material/AppBar";
 import IconButton from "@mui/material/IconButton";
diff --git a/gui/tsconfig.json b/gui/tsconfig.json
index a5db7f4..9ab7b8d 100644
--- a/gui/tsconfig.json
+++ b/gui/tsconfig.json
@@ -5,7 +5,6 @@
     "lib": ["ES2020", "DOM", "DOM.Iterable", "webworker"],
     "module": "ESNext",
     "skipLibCheck": true,
-
     "types": ["vite/client"],
     /* Bundler mode */
     "moduleResolution": "bundler",
@@ -14,13 +13,11 @@
     "isolatedModules": true,
     "noEmit": true,
     "jsx": "react-jsx",
-
     /* Linting */
     "strict": true,
     "noUnusedLocals": true,
     "noUnusedParameters": true,
     "noFallthroughCasesInSwitch": true,
-
     /* Imports */
     "baseUrl": "./src",
     "paths": {
@@ -37,14 +34,21 @@
       "@SpCore/gists/*": ["app/gists/*"],
       /* We are playing a bit fast and loose with the distinction */
       "@SpPages/*": ["app/pages/HomePage/*"],
-      "@SpStanc/*": ["app/Stanc/*", "app/CompilationServerConnectionControl/*"],
+      "@SpStanc/*": ["app/Stanc/*"],
       "@SpStanSampler/*": ["app/StanSampler/*"],
       "@SpUtil/*": ["app/util/*"],
       "@SpStanStats/*": ["app/util/stan_stats/*"],
       "@SpScripting/*": ["app/Scripting/*"],
-      "@SpCompileContext/*": ["app/CompileContext/*"]
+      "@SpCompilation/*": [
+        "app/Compilation/Context/*",
+        "app/Compilation/Control/*"
+      ]
     }
   },
   "include": ["src", "test"],
-  "references": [{ "path": "./tsconfig.node.json" }]
+  "references": [
+    {
+      "path": "./tsconfig.node.json"
+    }
+  ]
 }