One thing that may help is to try your best to ignore the fact that this is on a computer and try to do things exactly the way you're used to. Think of how you used to play. My guess is that it was with graph paper or possibly a dry-erase mat with physical dice. Try these steps: Player Characters/Monster Tokens: When you start a new campaign, click on the "Art Library" tab and search for "Sphere". The first thing that should come up is a white circle with a black background. Drag that on the grid somewhere and you should see a white circle with a bit of shading on the map. Think about this like a colored token (we used these a ton when we didn't have miniatures). Now double-click the circle. I window with a bunch of stuff and "Edit Token" at the top should appear. Ignore it...you wouldn't have all that stuff in your old game, you can figure it out later. There's one thing you're looking for..."Tint Color" at the lower left of the window. Click it, pick a color, and hit "Save Changes" at the lower right. Now you have a colored token, just like the colored marbles you could get at a hobby store. In an encounter you can use red for goblins, yellow for the ogre, and have a color for each player character. Want to differentiate the tokens a bit more? Double-click again, put a 0 in "Aura 1", choose a color, and click the check box next to "See" near "Aura 1" if you want your players to see it too. You now have a ton of combinations and you don't have to search for a bunch of tokens. You can also type a name of the token, i.e. "Goblin", click the check box next to "Show nameplate", and give players "See" permission next to name. This will label the tokens, making them easy to identify. Want a bigger monster? Drag the corners to make the token bigger. You can copy and paste them and they'll keep all the changes you made, so if you want several goblins you can cut and paste just like you would in Word. Last, in the options (double-click), note the "Controlled By" option. You can click this and select a player (or "All Players" for everyone) and they'll be able to move that token however they want. They can't delete or copy it, however, just move it, and change whatever properties you give them with the "Edit" boxes. This is handy for PC tokens. Maps Maps are even easier. Don't worry about map tiles or anything like that. You have a grid, and you can draw. Mouse over the paintbrush on the little bar at the top left, then select "Polygon/Line". Find the corner of a room you want to start, and (this is the key!) hold shift while clicking the corner. While still holding shift, click the end corner. You should now have a perfectly straight black line right along your grid (shift enables "snap-to-grid"). Here's the next trick...if you just hold shift and click farther on, your line will continue. If you go all the way back to your start point, you will "close" the line (in this case a polygon). If you want to stop a line without closing it, right click. You can now start a new line. You can change the color and thickness of lines with the options at the top left. Each line is now a separate object as well...if you click the icon that looks like a mouse pointer at the top (select) you can move them wherever you want, or delete them by selecting and hitting your Delete key. If you hold shift while moving they will continue to snap to grid, otherwise you can move them freely on the table. Finally, in order to really do a campaign, you'll need to add multiple maps. Click on the bookmark icon at the top right corner. A row with "Create New Page" and "Start", along with some squares above them, should show up. Click "Create New Page" to make a new map. Mouse over one of the pages and you'll see two things pop up, one on the left, the other on the right. The one on the left (Blue "gear" icon) opens up page settings where you can change the size of the map, plus a bunch of other stuff if you want. The key things are map size and "Delete" if you want to permanently remove a map. You can drag and drop the pages in any order you want. Click a page name to rename it. The only person who can see this is you as the GM. You'll also see a red "Players" bookmark on the Start page. You can drag and drop that bookmark to a new page and your players will all shift to that map. You'll need to copy and paste their tokens from the old page in order for them to get to the new page. Dice Dice macros are handy but not necessary. You can use the dice rolling tool to easily roll dice, and it even keeps track of your last couple of rolls so you can quickly reroll common rolls. I usually roll in chat, however, and there are a couple of things that make this easier. Just type /r (or /roll if you prefer) and the number and type of dice you want to roll, plus modifiers if you want. For example, /r 1d20+5 will roll a single d20 and add 5. If you have a fireball and want to roll 5d6, just type /r 5d6. Want to reroll it (or retype anything in chat)? Press the Up arrow key and you can scroll through previous chat commands. Character Sheets Chances are high your system can handle purely text-based character sheets. I've written literately hundreds of characters for D&D campaigns (and sometimes for fun) in notepad. To make a character sheet, go to the "Journal" tab, click the "+ Add" button next to "Characters", and you have a blank character sheet. Ignore 90% of what's on the sheet, like Avatar and Default token. The things you want are these: Name In Player's Journals Can Be Edited & Controlled By Bio & Info Ignore everything else for now, and don't even bother with the other tab. Name is the character's name. If you click the second two options, a list of everyone in your campaign will show up. This is who can see (first option) and who can modify (second option) those sheets. For the old school feel, you can choose "All Players" for In Player's Journals so everyone can read everyone else's character sheets, and just select the person who's character is represented in Can Be Edited & Controlled By . For the Bio & Info section fill this out with the text character sheet. You can copy and paste directly from notepad or Word as long as the formatting isn't too crazy. You can have your players fill out their own sheets here as well. Anyway, I hope that helps! It seems like a lot but it's really not that different from your old stuff. I think these are the core components you'll need to run a D&D game just like you could with pen and paper. Keep in mind that you'll still need to put in time for preparation before your game just like P&P roleplaying; don't expect Roll20 to let you skip this step. There's plenty of other stuff that can make your campaigns better than the pen and paper version and you'll probably figure them out as you mess with the program more. At first, however, I recommend sticking with this, maybe with the addition of a couple different tokens or adding hit point counters to tokens (click on of the three circles and enter a number, then + or - another number to increment or reduce the value, i.e. -5 to remove five hit points). Good luck and let us know how your game goes!