diff --git a/ee/bulk-operations-dashboard/api/controllers/software/edit-software.js b/ee/bulk-operations-dashboard/api/controllers/software/edit-software.js
index 983387100d..d97b0366a8 100644
--- a/ee/bulk-operations-dashboard/api/controllers/software/edit-software.js
+++ b/ee/bulk-operations-dashboard/api/controllers/software/edit-software.js
@@ -46,9 +46,23 @@ module.exports = {
       description: 'The provided replacement software\'s has the wrong extension.',
       statusCode: 400,
     },
+
     softwareUploadFailed: {
       description: 'The software upload failed'
-    }
+    },
+
+    softwareAlreadyExistsOnThisTeam: {
+      description: 'A software installer with this name already exists on the Fleet Instance',
+    },
+
+    couldNotReadVersion: {
+      description:'Fleet could not read version information from the provided software installer.'
+    },
+
+    softwareDeletionFailed: {
+      description: 'The specified software could not be deleted from the Fleet instance.',
+      statusCode: 409,
+    },
   },
 
 
@@ -167,7 +181,35 @@ module.exports = {
                   }
                 };
               },
-            })
+            }
+          )
+          .intercept({response: {status: 409}}, async (error)=>{// handles errors related to duplicate software items.
+            if(!software.id) {// If the software does not have an ID, it not stored in the app's database/s3 bucket, so we can safely delete the file in s3.
+              await sails.rm(sails.config.uploads.prefixForFileDeletion+softwareFd);
+            }
+            return {'softwareAlreadyExistsOnThisTeam': error};
+          })
+          .intercept({name: 'AxiosError', response: {status: 400}}, async (error)=>{// Handles errors related to malformed installer packages
+            if(!software.id) {// If the software does not have an ID, it not stored in the app's database/s3 bucket, so we can safely delete the file in s3.
+              await sails.rm(sails.config.uploads.prefixForFileDeletion+softwareFd);
+            }
+            let axiosError = error;
+            if(axiosError.response.data) {
+              if(axiosError.response.data.errors && _.isArray(axiosError.response.data.errors)){
+                if(axiosError.response.data.errors[0] && axiosError.response.data.errors[0].reason) {
+                  let errorMessageFromFleetInstance = axiosError.response.data.errors[0].reason;
+                  if(_.startsWith(errorMessageFromFleetInstance, `Couldn't add. Fleet couldn't read the version`)){
+                    return 'couldNotReadVersion';
+                  } else {
+                    sails.log.warn(`When attempting to upload a software installer, an unexpected error occurred communicating with the Fleet API. Error returned from Fleet API: ${errorMessageFromFleetInstance}`);
+                    return {'softwareUploadFailed': error};
+                  }
+                }
+              }
+            }
+            sails.log.warn(`When attempting to upload a software installer, an unexpected error occurred communicating with the Fleet API, ${require('util').inspect(error, {depth: 3})}`);
+            return {'softwareUploadFailed': error};
+          })
           .intercept(async (error)=>{
             // Note: with this current behavior, all errors from this upload are currently swallowed and a softwareUploadFailed response is returned.
             // FUTURE: Test to make sure that uploading duplicate software to a team results in a 409 response.
@@ -234,6 +276,33 @@ module.exports = {
                 };
               },
             })
+            .intercept({response: {status: 409}}, async (error)=>{// handles errors related to duplicate software items.
+              if(!software.id) {// If the software does not have an ID, it not stored in the app's database/s3 bucket, so we can safely delete the file in s3.
+                await sails.rm(sails.config.uploads.prefixForFileDeletion+softwareFd);
+              }
+              return {'softwareAlreadyExistsOnThisTeam': error};
+            })
+            .intercept({name: 'AxiosError', response: {status: 400}}, async (error)=>{// Handles errors related to malformed installer packages
+              if(!software.id) {// If the software does not have an ID, it not stored in the app's database/s3 bucket, so we can safely delete the file in s3.
+                await sails.rm(sails.config.uploads.prefixForFileDeletion+softwareFd);
+              }
+              let axiosError = error;
+              if(axiosError.response.data) {
+                if(axiosError.response.data.errors && _.isArray(axiosError.response.data.errors)){
+                  if(axiosError.response.data.errors[0] && axiosError.response.data.errors[0].reason) {
+                    let errorMessageFromFleetInstance = axiosError.response.data.errors[0].reason;
+                    if(_.startsWith(errorMessageFromFleetInstance, `Couldn't add. Fleet couldn't read the version`)){
+                      return 'couldNotReadVersion';
+                    } else {
+                      sails.log.warn(`When attempting to upload a software installer, an unexpected error occurred communicating with the Fleet API. Error returned from Fleet API: ${errorMessageFromFleetInstance}`);
+                      return {'softwareUploadFailed': error};
+                    }
+                  }
+                }
+              }
+              sails.log.warn(`When attempting to upload a software installer, an unexpected error occurred communicating with the Fleet API, ${require('util').inspect(error, {depth: 3})}`);
+              return {'softwareUploadFailed': error};
+            })
             .intercept(async (error)=>{
               // Note: with this current behavior, all errors from this upload are currently swallowed and a softwareUploadFailed response is returned.
               // FUTURE: Test to make sure that uploading duplicate software to a team results in a 409 response.
@@ -279,6 +348,11 @@ module.exports = {
             headers: {
               Authorization: `Bearer ${sails.config.custom.fleetApiToken}`,
             }
+          })
+          .intercept({raw:{statusCode: 409}}, (error)=>{
+            // If the Fleet instance's returns a 409 response, then the software is configured to be installed as
+            // part of the macOS setup experience, and must be removed before it can be deleted via API requests.
+            return {softwareDeletionFailed: error};
           });
         }
         // If the software had been previously undeployed, delete the installer in s3 and the db record.
@@ -289,9 +363,23 @@ module.exports = {
 
       } else if(software.teams && newTeamIds.length === 0) {
         // If this is a deployed software that is being unassigned, save information about the uploaded file in our s3 bucket.
+        for(let team of software.teams) {
+          // Now delete the software on the Fleet instance.
+          await sails.helpers.http.sendHttpRequest.with({
+            method: 'DELETE',
+            baseUrl: sails.config.custom.fleetBaseUrl,
+            url: `/api/v1/fleet/software/titles/${software.fleetApid}/available_for_install?team_id=${team.fleetApid}`,
+            headers: {
+              Authorization: `Bearer ${sails.config.custom.fleetApiToken}`,
+            }
+          })
+          .intercept({raw:{statusCode: 409}}, (error)=>{
+            // If the Fleet instance's returns a 409 response, then the software is configured to be installed as
+            // part of the macOS setup experience, and must be removed before it can be deleted via API requests.
+            return {softwareDeletionFailed: error};
+          });
+        }
         if(newSoftware) {
-          // remove the old copy.
-          // console.log('Removing old package for ',softwareName);
           await UndeployedSoftware.create({
             uploadFd: softwareFd,
             uploadMime: softwareMime,
@@ -315,17 +403,6 @@ module.exports = {
             uninstallScript,
           });
         }
-        // Now delete the software on the Fleet instance.
-        for(let team of software.teams) {
-          await sails.helpers.http.sendHttpRequest.with({
-            method: 'DELETE',
-            baseUrl: sails.config.custom.fleetBaseUrl,
-            url: `/api/v1/fleet/software/titles/${software.fleetApid}/available_for_install?team_id=${team.fleetApid}`,
-            headers: {
-              Authorization: `Bearer ${sails.config.custom.fleetApiToken}`,
-            }
-          });
-        }
 
       } else {
         // console.log('updating existing db record!');
diff --git a/ee/bulk-operations-dashboard/api/controllers/software/upload-software.js b/ee/bulk-operations-dashboard/api/controllers/software/upload-software.js
index 8a1ea99ed5..987bfe8792 100644
--- a/ee/bulk-operations-dashboard/api/controllers/software/upload-software.js
+++ b/ee/bulk-operations-dashboard/api/controllers/software/upload-software.js
@@ -35,6 +35,10 @@ module.exports = {
 
     softwareUploadFailed: {
       description:'An unexpected error occurred communicating with the Fleet API'
+    },
+
+    couldNotReadVersion: {
+      description:'Fleet could not read version information from the provided software installer.'
     }
 
   },
@@ -100,13 +104,32 @@ module.exports = {
             };
           }
         })
-        .intercept({response: {status: 409}}, async (error)=>{
+        .intercept({response: {status: 409}}, async (error)=>{// handles errors related to duplicate software items.
           await sails.rm(sails.config.uploads.prefixForFileDeletion+uploadedSoftware.fd);
           return {'softwareAlreadyExistsOnThisTeam': error};
         })
-        .intercept({name: 'AxiosError'}, async (error)=>{
+        .intercept({name: 'AxiosError', response: {status: 400}}, async (error)=>{// Handles errors related to malformed installer packages
           await sails.rm(sails.config.uploads.prefixForFileDeletion+uploadedSoftware.fd);
-          sails.log.warn(`When attempting to upload a software installer, an unexpected error occurred communicating with the Fleet API, ${require('util').inspect(error, {depth: 2})}`);
+          let axiosError = error;
+          if(axiosError.response.data) {
+            if(axiosError.response.data.errors && _.isArray(axiosError.response.data.errors)){
+              if(axiosError.response.data.errors[0] && axiosError.response.data.errors[0].reason) {
+                let errorMessageFromFleetInstance = axiosError.response.data.errors[0].reason;
+                if(_.startsWith(errorMessageFromFleetInstance, `Couldn't add. Fleet couldn't read the version`)){
+                  return 'couldNotReadVersion';
+                } else {
+                  sails.log.warn(`When attempting to upload a software installer, an unexpected error occurred communicating with the Fleet API. Error returned from Fleet API: ${errorMessageFromFleetInstance}`);
+                  return {'softwareUploadFailed': error};
+                }
+              }
+            }
+          }
+          sails.log.warn(`When attempting to upload a software installer, an unexpected error occurred communicating with the Fleet API, ${require('util').inspect(error, {depth: 3})}`);
+          return {'softwareUploadFailed': error};
+        })
+        .intercept({name: 'AxiosError'}, async (error)=>{// Handles any other error.
+          await sails.rm(sails.config.uploads.prefixForFileDeletion+uploadedSoftware.fd);
+          sails.log.warn(`When attempting to upload a software installer, an unexpected error occurred communicating with the Fleet API, ${require('util').inspect(error, {depth: 3})}`);
           return {'softwareUploadFailed': error};
         });
       }
diff --git a/ee/bulk-operations-dashboard/views/pages/software/software.ejs b/ee/bulk-operations-dashboard/views/pages/software/software.ejs
index eff9c8e989..dcc8b823aa 100644
--- a/ee/bulk-operations-dashboard/views/pages/software/software.ejs
+++ b/ee/bulk-operations-dashboard/views/pages/software/software.ejs
@@ -145,8 +145,11 @@
           <p class="mb-2"><strong>Teams</strong></p>
           <multifield :value="formData.teams" v-model="formData.newTeamIds" input-type="teamSelect" :select-options="teams" add-button-text="Add team"></multifield>
         </div>
-        <cloud-error v-if="cloudError && cloudError.exit === 'wrongInstallerExtension'">{{cloudError.responseInfo.body}}</cloud-error>
-        <cloud-error v-else-if="cloudError"></cloud-error>
+        <cloud-error class="mb-2"  v-if="cloudError && cloudError.exit === 'wrongInstallerExtension'">{{cloudError.responseInfo.body}}</cloud-error>
+        <cloud-error class="mb-2"  v-else-if="cloudError && cloudError === 'couldNotReadVersion'">The Fleet instance could not read version information from the provided software installer.</cloud-error>
+        <cloud-error class="mb-2"  v-else-if="cloudError && cloudError === 'softwareDeletionFailed'">This software has been configured to be installed as part of the macOS setup experience and cannot be removed from a team. Please remove this software from any teams you want to remove this from in the <a :href="`${fleetBaseUrl}/controls/setup-experience/install-software`" target="_blank">"Setup experience" tab of the Controls page</a> on your Fleet instance and try again </cloud-error>
+        <cloud-error  class="mb-2" v-else-if="cloudError && cloudError === 'softwareAlreadyExistsOnThisTeam'">An error occured when transfering this software to a new team. A software installer with the same name as this software already exists on one or more of the selected teams.</cloud-error>
+        <cloud-error class="mb-2"  v-else-if="cloudError"></cloud-error>
         <div purpose="modal-buttons" class="d-flex flex-row justify-content-end align-items-center">
           <ajax-button :syncing.sync="syncing" purpose="modal-button" type="submit">Save</ajax-button>
         </div>
@@ -189,6 +192,7 @@
         </div>
         <div class="invalid-feedback text-center" v-if="formErrors.teams">Please select the teams you want to deploy this software to.</div>
         <cloud-error v-if="cloudError && cloudError === 'softwareAlreadyExistsOnThisTeam'">A software with the same name as the uploaded software already exists on one or more of the selected teams.</cloud-error>
+        <cloud-error v-if="cloudError && cloudError === 'couldNotReadVersion'">The Fleet instance could not read version information from the provided software installer.</cloud-error>
         <cloud-error v-else-if="cloudError"></cloud-error>
         <div purpose="modal-buttons" class="d-flex flex-row justify-content-end align-items-center">
           <a purpose="cancel-button" @click="closeModal()">Cancel</a>