diff --git a/src/handlers/shared/check-unassigns.ts b/src/handlers/shared/check-unassigns.ts
new file mode 100644
index 00000000..7d2c3487
--- /dev/null
+++ b/src/handlers/shared/check-unassigns.ts
@@ -0,0 +1,20 @@
+import { Context } from "../../types";
+
+export async function wasPreviouslyUnassigned(
+  context: Context,
+  senderLogin: Context["payload"]["sender"],
+  issueNumber: Context["payload"]["issue"]
+): Promise<boolean> {
+  try {
+    const issueEvents = await context.octokit.issues.listEventsForTimeline({
+      owner: context.payload.repository.owner.login,
+      repo: context.payload.repository.name,
+      issue_number: issueNumber.id,
+    });
+
+    return issueEvents.data.some((event) => event.event === "unassigned" && event.event === senderLogin);
+  } catch (error) {
+    console.error("Error while checking previous assignment:", error);
+    return false;
+  }
+}
diff --git a/src/handlers/shared/start.ts b/src/handlers/shared/start.ts
index 42c87bc0..e8aeeb50 100644
--- a/src/handlers/shared/start.ts
+++ b/src/handlers/shared/start.ts
@@ -2,6 +2,7 @@ import { Context, ISSUE_TYPE, Label } from "../../types";
 import { isParentIssue, getAvailableOpenedPullRequests, getAssignedIssues, addAssignees, addCommentToIssue } from "../../utils/issue";
 import { calculateDurations } from "../../utils/shared";
 import { checkTaskStale } from "./check-task-stale";
+import { wasPreviouslyUnassigned } from "./check-unassigns";
 import { generateAssignmentComment } from "./generate-assignment-comment";
 import structuredMetadata from "./structured-metadata";
 import { assignTableComment } from "./table";
@@ -66,12 +67,18 @@ export async function start(context: Context, issue: Context["payload"]["issue"]
 
   const labels = issue.labels;
   const priceLabel = labels.find((label: Label) => label.name.startsWith("Price: "));
+  const isUnassigned = await wasPreviouslyUnassigned(context, sender, issue);
 
   if (!priceLabel) {
     await addCommentToIssue(context, "```diff\n! No price label is set to calculate the duration.\n```");
     throw new Error("No price label is set to calculate the duration");
   }
 
+  if (isUnassigned) {
+    await addCommentToIssue(context, "```diff\n! You were previously unassigned from this task. You cannot reassign yourself\n```");
+    throw new Error(`This user was unassigned from this task previously. Cannot auto assign`);
+  }
+
   const duration: number = calculateDurations(labels).shift() ?? 0;
 
   const { id, login } = sender;