There can be kind of a steep learning curve using WordPress. I know that when I first started blogging, I would spend a long time trying to get things to work, going back, and trying other things. So, I’m putting this out there in case anyone has an issue with posting images to the sidebar of their blog. I’ve included step-by-step pictures.
Step 1:
First of all, the image you want to use has to be in your WordPress Media Library.
So, go to your Dashboard and click on Media, and then Add New.
Step 2:
Click Select Files and choose the picture file you want to use from your computer.
Step 3:
Once the file is uploaded, it will appear as a thumbnail and a description on the bottom of the screen. I chose a picture of a Basset hound pup and a baby rabbit. Click on the Edit button next to it.
Step 4:
This will bring up the picture and its information on the right-hand side of the screen. Copy the entire File URL, making sure it ends with .jpg/.png/.gif or some file extension like that.
Step 5:
On the left side of the screen, hover over Appearance, and then click on Widgets.
Step 6:
Under the Widgets tab is a long list of various types of things you can put in the sidebar. The right-hand side of the screen shows what is already in your sidebar, in order. Find Image, down near the bottom of the list, and drag it to the place you’d like it on your sidebar. For this demonstration, I put mine last, underneath Blogs I like to read.
Once it is in place, a box will open up. First of all, paste the File URL we copied in Step 4 into the box marked Image URL.
Step 7:
From here, you can fill in a Widget title and picture caption , if you’d like. At the bottom in the section marked Link URL. Many people use this to go to Amazon.com or some other bookseller, if they put up a picture of their book cover (like I did with my short story Giselle). For my demonstration, I put in the URL to a Chinese comic site I like to read.
After this, click Save, then Close and everything is done. Now you can see the cute picture on the right side of my screen and click on it to go read some Chinese comics.
The Green-Walled Tower 
May 13th, 2014 at 11:14 pm
I also would have a difficult time of doing the media images when wanting to get a certain one up on my site, but one of most complicated features I had trouble with was working the menu items to get it all in a certain format and order. That was the most frustrating one for me to work with. But, all of them can take some practice before getting it all down the way one wants.
May 14th, 2014 at 7:58 am
I think I did it some other weird way. Great info! Thanks, David.
May 14th, 2014 at 8:37 am
I know lots of people know how to do this: it’s just for people starting out. I’m curious how you did it.
May 14th, 2014 at 12:30 pm
You’re right, when I first started with WP in late 2011 – the stairs were steep. I found the WP Tutorials pretty useful.
But sometimes there are software glitches – and these stump but also disappear – just like that!
All good wishes,
Eric
May 14th, 2014 at 3:51 pm
Thanks a million times david, i have asked quite a few people but none told me how to add one in the sidebar.
I will certainly try to use one or two… God bless your generous heart!
May 14th, 2014 at 4:45 pm
I’m glad you found it useful. 🙂
May 14th, 2014 at 11:11 pm
I’m going to tackle this…how generous are you to go to all this trouble. I really don’t know what to say, but thanks David. You’re a pal.
May 14th, 2014 at 11:27 pm
Bah, no trouble at all. 🙂 It was one of the trickiest things for me to figure out too so I’m sure it’s a common problem. Good luck~
May 14th, 2014 at 11:35 pm
Will let you know how I fare.
May 15th, 2014 at 12:46 am
Been here for an hour…followed your directions to a T but it still doesn’t appear. I’m thinking perhaps the file is too big. Even with your explicit step by step instructions, I still can’t do it. Is the bar open yet?
May 15th, 2014 at 7:31 am
Not sure why it’s not working but I feel your pain. Yesterday I was using GIMP for the first time to create a book cover. I don’t know what I was doing wrong but it kept not doing what I wanted at a certain point. They say it’s almost as good as Photoshop so it must have been me. Computers can be extremely frustrating at times.
May 17th, 2014 at 1:10 am
It’s your cyber student deserving a D as in dumb. I got the image off of Amazon thinking mine was too big, and I believe it was because it let me do everything but rather than the image it said on my Home Page, configure your widget image into widget area. I’m lost there Dave.
Ugh…hope you’re well. Raining here in New Yawk.