diff --git a/frontend/src/App.tsx b/frontend/src/App.tsx
index 0279555..c4c323b 100644
--- a/frontend/src/App.tsx
+++ b/frontend/src/App.tsx
@@ -180,6 +180,7 @@ const App = () => {
             {...{
               type: "chat",
               prompt: "What would you like to know about James?",
+              resetLabel: "chat",
               sessionId,
               connectionBase,
               setSnack,
diff --git a/frontend/src/Controls.tsx b/frontend/src/Controls.tsx
index adc7726..f74d1bf 100644
--- a/frontend/src/Controls.tsx
+++ b/frontend/src/Controls.tsx
@@ -487,7 +487,7 @@ const Controls = ({ sessionId, setSnack, connectionBase }: ControlsParams) => {
         <SystemInfoComponent systemInfo={systemInfo} />
       </AccordionActions>
     </Accordion>
-    <Button startIcon={<ResetIcon />} onClick={() => { reset(["history"], "History cleared."); }}>Clear Backstory History</Button>
+    <Button startIcon={<ResetIcon />} onClick={() => { reset(["history"], "History cleared."); }}>Delete Backstory History</Button>
     <Button onClick={() => { reset(["rags", "tools", "system_prompt", "message_history_length"], "Default settings restored.") }}>Reset system prompt, tunables, and RAG to defaults</Button>
   </div>);
 }
diff --git a/frontend/src/Conversation.tsx b/frontend/src/Conversation.tsx
index 83ca2b2..7a734b5 100644
--- a/frontend/src/Conversation.tsx
+++ b/frontend/src/Conversation.tsx
@@ -3,10 +3,8 @@ import TextField from '@mui/material/TextField';
 import Typography from '@mui/material/Typography';
 import Tooltip from '@mui/material/Tooltip';
 import Button from '@mui/material/Button';
-import IconButton from '@mui/material/IconButton';
 import Box from '@mui/material/Box';
 import SendIcon from '@mui/icons-material/Send';
-import ResetIcon from '@mui/icons-material/RestartAlt';
 import { SxProps, Theme } from '@mui/material';
 import PropagateLoader  from "react-spinners/PropagateLoader";
 
@@ -14,6 +12,7 @@ import { Message, MessageList, MessageData } from './Message';
 import { SetSnackType } from './Snack';
 import { ContextStatus } from './ContextStatus';
 import { useAutoScrollToBottom } from './AutoScroll';
+import { DeleteConfirmation } from './DeleteConfirmation';
 
 import './Conversation.css';
 
@@ -498,18 +497,10 @@ const Conversation = forwardRef<ConversationHandle, ConversationProps>(({
         }
 
         <Box key="jobActions" sx={{ display: "flex", justifyContent: "center", flexDirection: "row" }}>
-          <IconButton
-            sx={{ display: "flex", margin: 'auto 0px' }}
-            size="large"
-            edge="start"
-            color="inherit"
-            disabled={sessionId === undefined || processingMessage !== undefined}
-            onClick={() => { reset(); resetAction && resetAction(); }}
-          >
-            <Tooltip title={resetLabel || "Reset"} >
-              <ResetIcon />
-            </Tooltip>
-          </IconButton>
+          <DeleteConfirmation
+            label={resetLabel || "all data"}
+            disabled={sessionId === undefined || processingMessage !== undefined || filteredConversation.findIndex(m => m.role !== 'content') === -1}
+            onDelete={() => { reset(); resetAction && resetAction(); }} />
           <Tooltip title={actionLabel || "Send"}>
             <span style={{ display: "flex", flexGrow: 1 }}>
               <Button
diff --git a/frontend/src/DeleteConfirmation.tsx b/frontend/src/DeleteConfirmation.tsx
new file mode 100644
index 0000000..84e0900
--- /dev/null
+++ b/frontend/src/DeleteConfirmation.tsx
@@ -0,0 +1,88 @@
+import React, { useState } from 'react';
+import { 
+  IconButton, 
+  Dialog, 
+  DialogActions, 
+  DialogContent, 
+  DialogContentText, 
+  DialogTitle, 
+  Button, 
+  useMediaQuery,
+  Tooltip,
+} from '@mui/material';
+import { useTheme } from '@mui/material/styles';
+import ResetIcon from '@mui/icons-material/History';
+
+interface DeleteConfirmationProps {
+  onDelete: () => void,
+  disabled?: boolean,
+  label?: string,
+  color?: "inherit" | "default" | "primary" | "secondary" | "error" | "info" | "success" | "warning" | undefined
+};
+
+const DeleteConfirmation = (props : DeleteConfirmationProps) => {
+  const { onDelete, disabled, label, color } = props;
+  const [open, setOpen] = useState(false);
+  const theme = useTheme();
+  const fullScreen = useMediaQuery(theme.breakpoints.down('md'));
+
+  const handleClickOpen = () => {
+    setOpen(true);
+  };
+
+  const handleClose = () => {
+    setOpen(false);
+  };
+
+  const handleConfirmReset = () => {
+    onDelete();
+    setOpen(false);
+  };
+
+  return (
+    <>
+    <Tooltip title={label ? `Reset ${label}` : "Reset"} >
+      <IconButton 
+        aria-label="reset" 
+        onClick={handleClickOpen}
+        color={ color || "inherit" }
+        sx={{ display: "flex", margin: 'auto 0px' }}
+        size="large"
+        edge="start"
+        disabled={disabled}
+ >
+        <ResetIcon />
+      </IconButton>
+      </Tooltip>
+      
+      <Dialog
+        fullScreen={fullScreen}
+        open={open}
+        onClose={handleClose}
+        aria-labelledby="responsive-dialog-title"
+      >
+        <DialogTitle id="responsive-dialog-title">
+          {"Confirm Reset"}
+        </DialogTitle>
+        <DialogContent>
+          <DialogContentText>
+            This action will permanently reset { label ? label.toLocaleLowerCase() : "all data" } without the ability to recover it.
+            Are you sure you want to continue?
+          </DialogContentText>
+        </DialogContent>
+        <DialogActions>
+          <Button autoFocus onClick={handleClose}>
+            Cancel
+          </Button>
+          <Button onClick={handleConfirmReset} color="error" variant="contained">
+            Reset { label || "Everything" }
+          </Button>
+        </DialogActions>
+      </Dialog>
+    </>
+  );
+}
+
+export {
+  DeleteConfirmation
+};
\ No newline at end of file
diff --git a/frontend/src/ResumeBuilder.tsx b/frontend/src/ResumeBuilder.tsx
index 2818dda..cf9587a 100644
--- a/frontend/src/ResumeBuilder.tsx
+++ b/frontend/src/ResumeBuilder.tsx
@@ -119,12 +119,6 @@ const ResumeBuilder: React.FC<ResumeBuilderProps> = ({
       setHasJobDescription(true);
     }
 
-    /* If there is more than one message, it is user: "...JOB_DESCRIPTION...", assistant: "...stored..."
-     * which means a resume has been generated. */
-    if (reduced.length > 1) {
-      setHasResume(true);
-    }
-
     /* Filter out any messages which the server injected for state management */
     reduced = reduced.filter(m => m.display !== "hide");
 
@@ -253,6 +247,7 @@ const ResumeBuilder: React.FC<ResumeBuilderProps> = ({
           actionLabel: "Generate Resume",
           prompt: "Paste a job description, then click Generate...",
           multiline: true,
+          resetLabel: `job description${hasFacts ? ", resume, and fact check" : hasResume ? " and resume" : ""}`,
           messageFilter: filterJobDescriptionMessages,
           resetAction: resetJobDescription,
           onResponse: jobResponse,
@@ -269,6 +264,7 @@ const ResumeBuilder: React.FC<ResumeBuilderProps> = ({
           type: "job_description",
           actionLabel: "Send",
           prompt: "Ask a question about this job description...",
+          resetLabel: `job description${hasFacts ? ", resume, and fact check" : hasResume ? " and resume" : ""}`,
           messageFilter: filterJobDescriptionMessages,
           defaultPrompts: jobDescriptionQuestions,
           resetAction: resetJobDescription,
@@ -279,7 +275,7 @@ const ResumeBuilder: React.FC<ResumeBuilderProps> = ({
         }}
       />
     }
-  }, [connectionBase, filterJobDescriptionMessages, hasJobDescription, sessionId, setSnack, jobResponse, resetJobDescription]);
+  }, [connectionBase, filterJobDescriptionMessages, hasJobDescription, sessionId, setSnack, jobResponse, resetJobDescription, hasFacts, hasResume]);
 
   /**
    * Renders the resume view with loading indicator
@@ -299,6 +295,7 @@ const ResumeBuilder: React.FC<ResumeBuilderProps> = ({
           actionLabel: "Fact Check",
           multiline: true,
           type: "resume",
+          resetLabel: `job description${hasFacts ? ", resume, and fact check" : hasResume ? " and resume" : ""}`,
           messageFilter: filterResumeMessages,
           onResponse: resumeResponse,
           resetAction: resetResume,
@@ -314,6 +311,7 @@ const ResumeBuilder: React.FC<ResumeBuilderProps> = ({
           type: "resume",
           actionLabel: "Send",
           prompt: "Ask a question about this job resume...",
+          resetLabel: `job description${hasFacts ? ", resume, and fact check" : hasResume ? " and resume" : ""}`,
           messageFilter: filterResumeMessages,
           defaultPrompts: resumeQuestions,
           resetAction: resetResume,
@@ -324,7 +322,7 @@ const ResumeBuilder: React.FC<ResumeBuilderProps> = ({
         }}
       />
     }
-  }, [connectionBase, filterResumeMessages, hasFacts, sessionId, setSnack, resumeResponse, resetResume]);
+  }, [connectionBase, filterResumeMessages, hasFacts, sessionId, setSnack, resumeResponse, resetResume, hasResume]);
 
   /**
    * Renders the fact check view
@@ -342,6 +340,7 @@ const ResumeBuilder: React.FC<ResumeBuilderProps> = ({
         type: "fact_check",
         actionLabel: "Send",
         prompt: "Ask a question about any discrepencies...",
+        resetLabel: `job description${hasFacts ? ", resume, and fact check" : hasResume ? " and resume" : ""}`,
         messageFilter: filterFactsMessages,
         defaultPrompts: factsQuestions,
         resetAction: resetFacts,
@@ -351,7 +350,7 @@ const ResumeBuilder: React.FC<ResumeBuilderProps> = ({
         setSnack,
       }}
     />
-  }, [connectionBase, sessionId, setSnack, factsResponse, filterFactsMessages, resetFacts]);
+  }, [connectionBase, sessionId, setSnack, factsResponse, filterFactsMessages, resetFacts, hasResume, hasFacts]);
 
   /**
    * Gets the appropriate content based on active state for Desktop
diff --git a/src/server.py b/src/server.py
index e18332e..42309de 100644
--- a/src/server.py
+++ b/src/server.py
@@ -579,8 +579,8 @@ class WebServer:
                         case "history":
                             reset_map = {
                                 "job_description": ("job_description", "resume", "fact_check"),
-                                "resume": ("resume", "fact_check"),
-                                "fact_check": ("fact_check",),
+                                "resume": ("job_description", "resume", "fact_check"),
+                                "fact_check": ("job_description", "resume", "fact_check"),
                                 "chat": ("chat",),
                             }
                             resets = reset_map.get(session_type, ())