diff --git a/R/chat-structured.R b/R/chat-structured.R
index 4ef25a1f..0c240a84 100644
--- a/R/chat-structured.R
+++ b/R/chat-structured.R
@@ -1,13 +1,63 @@
-extract_data <- function(turn, type, convert = TRUE, needs_wrapper = FALSE) {
+extract_data <- function(
+  turn,
+  type,
+  convert = TRUE,
+  needs_wrapper = FALSE,
+  prompt_index = NULL
+) {
   is_json <- map_lgl(turn@contents, S7_inherits, ContentJson)
   n <- sum(is_json)
-  if (n != 1) {
-    cli::cli_abort("Data extraction failed: {n} data results recieved.")
+  if (n == 0) {
+    cli::cli_abort("Data extraction failed: 0 data results received.")
+  } else if (n == 1) {
+    # Normal case - exactly 1 JSON object
+    json <- turn@contents[[which(is_json)]]
+    out <- json@value
+  } else if (n == 2) {
+    # Check if the two JSON objects are identical (duplicate case)
+    json_indices <- which(is_json)
+    json1 <- turn@contents[[json_indices[1]]]
+    json2 <- turn@contents[[json_indices[2]]]
+    val1 <- json1@value
+    val2 <- json2@value
+    if (identical(val1, val2)) {
+      # Duplicate case - use the first one
+      index_msg <- if (!is.null(prompt_index)) {
+        paste0(" (prompt ", prompt_index, ")")
+      } else {
+        ""
+      }
+      warning(
+        "Found duplicate JSON responses, using the first one",
+        index_msg,
+        ".",
+        call. = FALSE,
+        immediate. = TRUE
+      )
+      out <- val1
+    } else {
+      # Different JSON objects - use the last one (likely the final response)
+      index_msg <- if (!is.null(prompt_index)) {
+        paste0(" (prompt ", prompt_index, ")")
+      } else {
+        ""
+      }
+      warning(
+        "Found multiple different JSON responses, using the last one",
+        index_msg,
+        ".",
+        call. = FALSE,
+        immediate. = TRUE
+      )
+      out <- val2
+    }
+  } else {
+    # More than 2 JSON objects - this is unexpected
+    cli::cli_abort(
+      "Data extraction failed: {n} data results received. Expected 1 or 2."
+    )
   }
 
-  json <- turn@contents[[which(is_json)]]
-  out <- json@value
-
   if (needs_wrapper) {
     out <- out$wrapper
     type <- type@properties[[1]]
diff --git a/R/parallel-chat.R b/R/parallel-chat.R
index d77b77e0..35ba2164 100644
--- a/R/parallel-chat.R
+++ b/R/parallel-chat.R
@@ -170,12 +170,13 @@ multi_convert <- function(
 ) {
   needs_wrapper <- type_needs_wrapper(type, provider)
 
-  rows <- map(turns, \(turn) {
+  rows <- imap(turns, \(turn, idx) {
     extract_data(
       turn = turn,
       type = wrap_type_if_needed(type, needs_wrapper),
       convert = FALSE,
-      needs_wrapper = needs_wrapper
+      needs_wrapper = needs_wrapper,
+      prompt_index = idx
     )
   })
 
diff --git a/tests/testthat/_snaps/chat-structured.md b/tests/testthat/_snaps/chat-structured.md
deleted file mode 100644
index 6812f46f..00000000
--- a/tests/testthat/_snaps/chat-structured.md
+++ /dev/null
@@ -1,8 +0,0 @@
-# useful error if no ContentJson
-
-    Code
-      extract_data(turn)
-    Condition
-      Error in `extract_data()`:
-      ! Data extraction failed: 0 data results recieved.
-
diff --git a/tests/testthat/test-chat-structured.R b/tests/testthat/test-chat-structured.R
index 95889ea5..5fa16ca6 100644
--- a/tests/testthat/test-chat-structured.R
+++ b/tests/testthat/test-chat-structured.R
@@ -2,7 +2,11 @@
 
 test_that("useful error if no ContentJson", {
   turn <- Turn("assistant", list(ContentText("Hello")))
-  expect_snapshot(extract_data(turn), error = TRUE)
+  expect_error(
+    extract_data(turn),
+    "Data extraction failed: 0 data results received.",
+    fixed = TRUE
+  )
 })
 
 test_that("can extract data from ContentJson", {
@@ -24,6 +28,92 @@ test_that("can extract data when wrapper is used", {
   expect_equal(extract_data(turn, type, needs_wrapper = TRUE), list(x = 1))
 })
 
+test_that("handles duplicate identical JSON responses", {
+  # This test covers the Bedrock duplicate JSON issue
+  json_data <- list(name = "John", age = 25)
+  turn <- Turn(
+    "assistant",
+    list(
+      ContentJson(json_data),
+      ContentJson(json_data) # Identical duplicate
+    )
+  )
+  type <- type_object(name = type_string(), age = type_integer())
+  # Should warn about duplicates and use the first one
+  expect_warning(
+    result <- extract_data(turn, type),
+    "Found duplicate JSON responses, using the first one"
+  )
+  expect_equal(result, list(name = "John", age = 25))
+})
+
+test_that("handles duplicate identical JSON responses with prompt index", {
+  # Test that prompt index is included in warning message
+  json_data <- list(score = 42)
+  turn <- Turn(
+    "assistant",
+    list(
+      ContentJson(json_data),
+      ContentJson(json_data)
+    )
+  )
+  type <- type_object(score = type_integer())
+  expect_warning(
+    extract_data(turn, type, prompt_index = 3),
+    "Found duplicate JSON responses, using the first one \\(prompt 3\\)"
+  )
+})
+
+test_that("handles different JSON responses", {
+  # This test covers the case where two different JSON objects are returned
+  turn <- Turn(
+    "assistant",
+    list(
+      ContentJson(list(name = "John", age = 25)),
+      ContentJson(list(name = "Jane", age = 30)) # Different data
+    )
+  )
+  type <- type_object(name = type_string(), age = type_integer())
+  # Should warn about multiple responses and use the last one
+  expect_warning(
+    result <- extract_data(turn, type),
+    "Found multiple different JSON responses, using the last one"
+  )
+  expect_equal(result, list(name = "Jane", age = 30))
+})
+
+test_that("handles different JSON responses with prompt index", {
+  turn <- Turn(
+    "assistant",
+    list(
+      ContentJson(list(value = 1)),
+      ContentJson(list(value = 2))
+    )
+  )
+  type <- type_object(value = type_integer())
+  expect_warning(
+    extract_data(turn, type, prompt_index = 5),
+    "Found multiple different JSON responses, using the last one \\(prompt 5\\)"
+  )
+})
+
+test_that("errors on more than 2 JSON responses", {
+  # Should error if there are more than 2 JSON objects
+  turn <- Turn(
+    "assistant",
+    list(
+      ContentJson(list(x = 1)),
+      ContentJson(list(x = 2)),
+      ContentJson(list(x = 3))
+    )
+  )
+  type <- type_object(x = type_integer())
+  expect_error(
+    extract_data(turn, type),
+    "Data extraction failed: 3 data results received. Expected 1 or 2."
+  )
+})
+
 # Type coercion ---------------------------------------------------------------
 
 test_that("optional base types (scalars) stay as NULL", {