diff --git a/apps/app/src/paths/Activities.tsx b/apps/app/src/paths/Activities.tsx
index 950f459f1..37a50e7ea 100644
--- a/apps/app/src/paths/Activities.tsx
+++ b/apps/app/src/paths/Activities.tsx
@@ -487,6 +487,7 @@ export function Activities() {
       },
       onDelete: () => {
         setSettingsContentId(cardSelections.ids.values().next().value ?? null);
+        cardSelections.clear();
         deleteContentOnOpen();
       },
     });
diff --git a/apps/app/src/views/CompoundActivityEditor.tsx b/apps/app/src/views/CompoundActivityEditor.tsx
index f0a277132..5e521e8a8 100644
--- a/apps/app/src/views/CompoundActivityEditor.tsx
+++ b/apps/app/src/views/CompoundActivityEditor.tsx
@@ -443,6 +443,7 @@ export function CompoundActivityEditor({
           (c) => c.contentId === cardSelections.ids.values().next().value,
         );
         if (selectedContent) {
+          cardSelections.clear();
           setContentToDelete(selectedContent);
           deleteContentOnOpen();
         }
diff --git a/packages/e2e-tests/e2e/Content Lists/deleteFromCompoundActivity.cy.ts b/packages/e2e-tests/e2e/Content Lists/deleteFromCompoundActivity.cy.ts
new file mode 100644
index 000000000..2d7b50816
--- /dev/null
+++ b/packages/e2e-tests/e2e/Content Lists/deleteFromCompoundActivity.cy.ts	
@@ -0,0 +1,170 @@
+describe("Delete from compound activity tests", { tags: ["@group3"] }, () => {
+  it("Delete document from problem set", () => {
+    cy.loginAsTestUser();
+
+    cy.createContent({ name: "Problem Set 1", contentType: "sequence" }).then(
+      (sequenceId) => {
+        cy.createContent({
+          name: "Document P1",
+          contentType: "singleDoc",
+          parentId: sequenceId,
+        });
+        cy.createContent({
+          name: "Document P2",
+          contentType: "singleDoc",
+          parentId: sequenceId,
+        });
+        cy.createContent({
+          name: "Document P3",
+          contentType: "singleDoc",
+          parentId: sequenceId,
+        });
+      },
+    );
+
+    cy.visit("/");
+    cy.get('[data-test="My Activities"]').click();
+
+    cy.get(`[data-test="Content Card"]`).should("have.length", 1);
+    cy.get(`[data-test="Content Card"]`)
+      .eq(0)
+      .should("contain.text", "Problem Set 1")
+      .click();
+
+    cy.get('[data-test="Editable Title"]').should("have.text", "Problem Set 1");
+    cy.get(`[data-test="Content Card"]`).should("have.length", 3);
+
+    cy.get('[data-test="Card Select"]').eq(0).click();
+    cy.get('[aria-label="Move to trash"]').click();
+    cy.get('[data-test="Confirm Delete Message"]').should(
+      "contain.text",
+      "Document P1",
+    );
+    cy.get('[data-test="Delete Button"]').click();
+
+    cy.get(`[data-test="Content Card"]`).should("have.length", 2);
+    cy.get(`[data-test="Content Card"]`)
+      .eq(0)
+      .should("contain.text", "Document P2");
+  });
+
+  it("Delete multiple documents sequentially from problem set", () => {
+    cy.loginAsTestUser();
+
+    cy.createContent({ name: "Problem Set 1", contentType: "sequence" }).then(
+      (sequenceId) => {
+        cy.createContent({
+          name: "Document P1",
+          contentType: "singleDoc",
+          parentId: sequenceId,
+        });
+        cy.createContent({
+          name: "Document P2",
+          contentType: "singleDoc",
+          parentId: sequenceId,
+        });
+        cy.createContent({
+          name: "Document P3",
+          contentType: "singleDoc",
+          parentId: sequenceId,
+        });
+      },
+    );
+
+    cy.visit("/");
+    cy.get('[data-test="My Activities"]').click();
+
+    cy.get(`[data-test="Content Card"]`)
+      .eq(0)
+      .should("contain.text", "Problem Set 1")
+      .click();
+
+    cy.get('[data-test="Editable Title"]').should("have.text", "Problem Set 1");
+    cy.get(`[data-test="Content Card"]`).should("have.length", 3);
+
+    // Delete Document P1
+    cy.log("Delete Document P1");
+    cy.get('[data-test="Card Select"]').eq(0).click();
+    cy.get('[aria-label="Move to trash"]').click();
+    cy.get('[data-test="Confirm Delete Message"]').should(
+      "contain.text",
+      "Document P1",
+    );
+    cy.get('[data-test="Delete Button"]').click();
+
+    cy.get(`[data-test="Content Card"]`).should("have.length", 2);
+    cy.get(`[data-test="Content Card"]`)
+      .eq(0)
+      .should("contain.text", "Document P2");
+    cy.get(`[data-test="Content Card"]`)
+      .eq(1)
+      .should("contain.text", "Document P3");
+
+    // Delete Document P2 (second deletion from same problem set)
+    cy.log("Delete Document P2");
+    cy.get('[data-test="Card Select"]').eq(0).click();
+    cy.get('[aria-label="Move to trash"]').click();
+    cy.get('[data-test="Confirm Delete Message"]').should(
+      "contain.text",
+      "Document P2",
+    );
+    cy.get('[data-test="Delete Button"]').click();
+
+    cy.get(`[data-test="Content Card"]`).should("have.length", 1);
+    cy.get(`[data-test="Content Card"]`)
+      .eq(0)
+      .should("contain.text", "Document P3");
+  });
+
+  it("Delete all documents from problem set", () => {
+    cy.loginAsTestUser();
+
+    cy.createContent({
+      name: "Empty Problem Set",
+      contentType: "sequence",
+    }).then((sequenceId) => {
+      cy.createContent({
+        name: "Document A",
+        contentType: "singleDoc",
+        parentId: sequenceId,
+      });
+      cy.createContent({
+        name: "Document B",
+        contentType: "singleDoc",
+        parentId: sequenceId,
+      });
+    });
+
+    cy.visit("/");
+    cy.get('[data-test="My Activities"]').click();
+
+    cy.get(`[data-test="Content Card"]`)
+      .eq(0)
+      .should("contain.text", "Empty Problem Set")
+      .click();
+
+    cy.get('[data-test="Editable Title"]').should(
+      "have.text",
+      "Empty Problem Set",
+    );
+    cy.get(`[data-test="Content Card"]`).should("have.length", 2);
+
+    // Delete Document A
+    cy.get('[data-test="Card Select"]').eq(0).click();
+    cy.get('[aria-label="Move to trash"]').click();
+    cy.get('[data-test="Delete Button"]').click();
+
+    cy.get(`[data-test="Content Card"]`).should("have.length", 1);
+
+    // Delete Document B
+    cy.get('[data-test="Card Select"]').eq(0).click();
+    cy.get('[aria-label="Move to trash"]').click();
+    cy.get('[data-test="Confirm Delete Message"]').should(
+      "contain.text",
+      "Document B",
+    );
+    cy.get('[data-test="Delete Button"]').click();
+
+    cy.get(`[data-test="Content Card"]`).should("have.length", 0);
+  });
+});