diff --git a/charts/budibase/values.yaml b/charts/budibase/values.yaml
index 32c241807c..a9dbcd426b 100644
--- a/charts/budibase/values.yaml
+++ b/charts/budibase/values.yaml
@@ -103,7 +103,7 @@ globals:
   google:
     clientId: "" 
     secret: ""
-  automationMaxIterations: "0"
+  automationMaxIterations: "500"
 
   createSecrets: true # creates an internal API key, JWT secrets and redis password for you
 
diff --git a/packages/server/src/automations/automationUtils.js b/packages/server/src/automations/automationUtils.js
index 9360840efd..0d858741dd 100644
--- a/packages/server/src/automations/automationUtils.js
+++ b/packages/server/src/automations/automationUtils.js
@@ -1,4 +1,5 @@
 const { getTable } = require("../api/controllers/table/utils")
+const { findHBSBlocks } = require("@budibase/string-templates")
 
 /**
  * When values are input to the system generally they will be of type string as this is required for template strings.
@@ -74,3 +75,14 @@ exports.getError = err => {
   }
   return typeof err !== "string" ? err.toString() : err
 }
+
+exports.substituteLoopStep = (hbsString, substitute) => {
+  let blocks = findHBSBlocks(hbsString)
+  for (let block of blocks) {
+    let oldBlock = block
+    block = block.replace(/loop/, substitute)
+    hbsString = hbsString.replace(new RegExp(oldBlock, "g"), block)
+  }
+
+  return hbsString
+}
diff --git a/packages/server/src/automations/steps/loop.js b/packages/server/src/automations/steps/loop.js
index 14c58aee6a..238f4b5746 100644
--- a/packages/server/src/automations/steps/loop.js
+++ b/packages/server/src/automations/steps/loop.js
@@ -32,7 +32,7 @@ exports.definition = {
       properties: {
         items: {
           customType: "item",
-          description: "the item currently being executed",
+          description: "The item currently being executed",
         },
         success: {
           type: "boolean",
@@ -43,7 +43,7 @@ exports.definition = {
           descriptions: "The amount of times the block ran",
         },
       },
-      required: ["success"],
+      required: ["success, items, iterations"],
     },
   },
   type: "LOGIC",
diff --git a/packages/server/src/constants/index.js b/packages/server/src/constants/index.js
index cf89f1fe99..8dbac5c1b9 100644
--- a/packages/server/src/constants/index.js
+++ b/packages/server/src/constants/index.js
@@ -190,5 +190,11 @@ exports.WebhookType = {
   AUTOMATION: "automation",
 }
 
+exports.AutomationErrors = {
+  INCORRECT_TYPE: "INCORRECT_TYPE",
+  MAX_ITERATIONS: "MAX_ITERATIONS_REACHED",
+  FAILURE_CONDITION: "FAILURE_CONDITION_MET",
+}
+
 // pass through the list from the auth/core lib
 exports.ObjectStoreBuckets = ObjectStoreBuckets
diff --git a/packages/server/src/threads/automation.js b/packages/server/src/threads/automation.js
index aef8263274..db462f5a8d 100644
--- a/packages/server/src/threads/automation.js
+++ b/packages/server/src/threads/automation.js
@@ -8,7 +8,7 @@ const { DocumentTypes } = require("../db/utils")
 const { doInTenant } = require("@budibase/backend-core/tenancy")
 const { definitions: triggerDefs } = require("../automations/triggerInfo")
 const { doInAppContext, getAppDB } = require("@budibase/backend-core/context")
-
+const { AutomationErrors } = require("../constants")
 const FILTER_STEP_ID = actions.ACTION_DEFINITIONS.FILTER.stepId
 const LOOP_STEP_ID = actions.ACTION_DEFINITIONS.LOOP.stepId
 
@@ -146,7 +146,7 @@ class Orchestrator {
               typeof newInput.binding !== "string")
           ) {
             this.updateContextAndOutput(loopStepNumber, step, tempOutput, {
-              status: "INCORRECT_TYPE",
+              status: AutomationErrors.INCORRECT_TYPE,
               success: false,
             })
             loopSteps = null
@@ -156,18 +156,26 @@ class Orchestrator {
 
           // The "Loop" binding in the front end is "fake", so replace it here so the context can understand it
           // Pretty hacky because we need to account for the row object
-          for (let key in originalStepInput) {
-            if (key === "row") {
-              for (let val in originalStepInput["row"]) {
-                originalStepInput["row"][val] = originalStepInput["row"][
-                  val
-                ].replace(/loop/, `steps.${loopStepNumber}`)
+          for (let [key, value] of Object.entries(originalStepInput)) {
+            if (typeof value === "object") {
+              for (let [innerKey, innerValue] of Object.entries(
+                originalStepInput[key]
+              )) {
+                if (typeof innerValue === "string") {
+                  originalStepInput[key][innerKey] =
+                    automationUtils.substituteLoopStep(
+                      innerValue,
+                      `steps.${loopStepNumber}`
+                    )
+                }
               }
             } else {
-              originalStepInput[key] = originalStepInput[key].replace(
-                /loop/,
-                `steps.${loopStepNumber}`
-              )
+              if (typeof value === "string") {
+                originalStepInput[key] = automationUtils.substituteLoopStep(
+                  value,
+                  `steps.${loopStepNumber}`
+                )
+              }
             }
           }
 
@@ -176,7 +184,7 @@ class Orchestrator {
             index === loopStep.inputs.iterations
           ) {
             this.updateContextAndOutput(loopStepNumber, step, tempOutput, {
-              status: "MAX_ITERATIONS_REACHED",
+              status: AutomationErrors.MAX_ITERATIONS,
               success: true,
             })
             loopSteps = null
@@ -189,7 +197,7 @@ class Orchestrator {
             loopStep.inputs.failure
           ) {
             this.updateContextAndOutput(loopStepNumber, step, tempOutput, {
-              status: "FAILURE_CONDITION_MET",
+              status: AutomationErrors.FAILURE_CONDITION,
               success: false,
             })
             loopSteps = null